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Preparation method of 3,5-di (trifluoromethyl) benzoyl chloride and new 3,5-di trihalomethyl benzoylate A and 3,5-dimethyl benzoylate A

A technology of benzoyl chloride and trifluoromethyl, used in the preparation of 3,5-bis(trifluoromethyl)benzoyl chloride and new 3,5-bis(trihalomethyl)- and 3, In the field of 5-dimethylbenzoyl halide, it can solve problems such as huge expenses

Inactive Publication Date: 2005-08-24
LANXESS DEUTDCHLAND GMBH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In addition, there is the risk of exothermic decomposition of metal-trifluoromethyl-substituted phenylmagnesium and -lithium compounds, which again requires huge expenditures to ensure control

Method used

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  • Preparation method of 3,5-di (trifluoromethyl) benzoyl chloride and new 3,5-di trihalomethyl benzoylate A and 3,5-dimethyl benzoylate A
  • Preparation method of 3,5-di (trifluoromethyl) benzoyl chloride and new 3,5-di trihalomethyl benzoylate A and 3,5-dimethyl benzoylate A
  • Preparation method of 3,5-di (trifluoromethyl) benzoyl chloride and new 3,5-di trihalomethyl benzoylate A and 3,5-dimethyl benzoylate A

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0070] 3,5-Dimethylbenzoyl chloride

[0071] First, 1000 g of 3,5-dimethylbenzoic acid in 450 ml of toluene was placed in a 4-liter flat-bottomed reaction vessel, and 80 ml of thionyl chloride was added dropwise at 60° C. for 2 hours under stirring to generate gas. The mixture was then heated to boiling (internal temperature 102°C) and refluxed for 2 hours. Excess thionyl chloride and some toluene were then distilled off at atmospheric pressure at a top temperature of up to 102° C. during 1.5 hours. The mixture was allowed to cool to 80°C and the toluene was distilled off, this time at 20 mbar. The residue was distilled off at 20 mbar up to a boiling point of 110° C. (in the still) column. The residue obtained was 1092 g (96.7% of theory) of 3,5-dimethylbenzoyl chloride.

Embodiment 2

[0073] 3,5-Bis(trichloromethyl)benzoyl chloride

[0074] At 120°C, 1092g of 3,5-dimethylbenzoyl chloride was first added to a reaction vessel equipped with an air-cooled UV immersion lamp. Under UV radiation, a total amount of 4340g of chlorine was introduced during 61 hours, and the temperature rose steadily. up to 180°C. At this point 100% of the starting material had reacted according to GC analysis. After blowing off the excess chlorine with nitrogen, 2390 g (98.1% of theory) of 3,5-bis(trichloromethyl)benzoyl chloride remained.

Embodiment 3

[0076] 3,5-bis(trifluoromethyl)benzoyl fluoride

[0077] First, 990 ml of anhydrous hydrofluoric acid were added to a 5 liter stainless steel stirred autoclave equipped with a sloped condenser (operated at -10°C with coolant) and a pressure regulator. Then, 1126 g of 3,5-bis(trichloromethyl)benzoyl chloride were added dropwise during 30 minutes at -5 to 0°C, with only slight generation of hydrogen chloride gas. Allow the temperature to rise to +20°C. When the slight gas evolution had ended (after 1.5 hours), 68 g of titanium tetrachloride were added during 40 minutes. When the new gas evolution subsides (after 2 hours), seal the equipment, inject nitrogen to 10 bar, gradually heat the equipment to 140° C., and continuously depressurize the generated hydrogen chloride at 25 bar. After 11 hours at 140°C, the reaction was complete. The autoclave was cooled and decompressed, excess hydrogen fluoride (248 g) was distilled off at atmospheric pressure, and the residue was distille...

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Abstract

Preparation of 3,5-bis-(trifluoromethyl)-benzoyl chlorides (I) involves converting a 3,5-dimethyl-benzoic acid (V) into the acid chloride (IV), subjecting the side-chains to radical chlorination, fluorinating with anhydrous hydrogen fluoride and / or antimony pentafluoride to give a 3,5-bis-(trifluoromethyl)-benzoyl fluoride and reacting with silicon tetrachloride in presence of another Lewis acid. Preparation of 3,5-bis-(trifluoromethyl)-benzoyl chlorides of formula (I) involves: (1) converting a 3,5-dimethyl-benzoic acid of formula (V) into the corresponding acid chloride of formula (IV); (2) subjecting the side-chains to complete radical chlorination to give a 3,5-bis-(trichloromethyl)-benzoyl chloride of formula (III); (3) fluorinating with anhydrous hydrogen fluoride and / or antimony pentafluoride to give a 3,5-bis-(trifluoromethyl)-benzoyl fluoride of formula (II); and (4) reacting with silicon tetrachloride in presence of another Lewis acid. [Image] X : H, F or Cl. Independent claims are included for the intermediates (III; X = F or Cl) and (IV; X = F or Cl) as new compounds.

Description

technical field [0001] The present invention relates to a process for the preparation of 3,5-bis(trifluoromethyl)benzoyl chloride from the corresponding 3,5-dimethylbenzoic acid and novel 3,5-bis( Trihalomethyl)- and 3,5-dimethylbenzoyl halides. Hereinafter, 3,5-bis(trifluoromethyl)-benzoyl chloride is also referred to as BTBs. Background technique [0002] BTBs are intermediates in the preparation of pharmaceutical and agrochemical active ingredients as well as photoresist ingredients. [0003] The preparation of BTBs from the corresponding 3,5-bis(trifluoromethyl)benzoic acid by chlorination is known (see, e.g., J.Med.Chem. 38 , 3106 (1995)). This acid can be obtained by two different methods, namely, [0004] a) Metallization of 1-bromo-3,5-bis(trifluoromethyl)benzene with magnesium or lithium (see, Bull.Soc.Chim.Fr. 1962 (587) and Chem. Ber. 129 , 233 (1996)), followed by reaction with carbon dioxide, or with carbon monoxide and water in the presence of a palladiu...

Claims

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Application Information

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IPC IPC(8): C07C51/58C07B61/00C07C51/60C07C51/62C07C63/00C07C63/68C07C63/70
CPCC07C51/62C07C51/60C07C63/70C07C63/72
Inventor A·马霍尔德J·斯特尔廷
Owner LANXESS DEUTDCHLAND GMBH
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