Method for converting carboxylic acid groups to trichloromethyl groups

• US 4,634,771 A
• Filed: 07/25/1985
• Issued: 01/06/1987
• Est. Priority Date: 07/25/1985
• Status: Expired due to Fees

• Current Assignee: ICI America Incorporated (Nouryon BV)
• Original Assignee: Stauffer Chemical Company (Nouryon BV)
• Inventors: Heather, James B., Shim, Kyung S., Toy, Arthur D. F.
• Primary Examiner(s): Jiles, Henry R.
• Assistant Examiner(s): Whittenbaugh, Robert C.
• Application Number:
  US06/759,003
• Time in Patent Office: 530 Days
• Field of Search: 546/346, 546/345, 546/286, 546/297, 546/302, 570/185, 558/411, 568/630, 568/635, 568/716, 568/936, 568/927
• US Class Current: 546/286
• CPC Class Codes: C07D 213/26 Radicals substituted by halogen atoms or nitro radicals
• CPC Class Codes: C07D 213/61 Halogen atoms or nitro radicals

Abstract

There is disclosed a method for the conversion of a carboxylic acid group on the ring of an aromatic or N-heteroaromatic compound to a trichloromethyl group which comprises contacting the aromatic or N-heteroaromatic compound with a phenylphosphonous dichloride, phosphorus trichloride and chlorine.

Claims

1. A method for the conversion of a carboxylic acid group on the ring of an aromatic or N-heteroaromatic compound to a trichloromethyl group which comprises contacting at a temperature of from about 100°

C. to about 250°

C. the aromatic or N-heteroaromatic compound with (i) from about 0.5 to about 2.0 molar equivalents of phenylphosphonous dichloride per carboxylic acid group to be converted, (ii) phosphorus trichloride, and (iii) chlorine;

wherein the molar ratio of chlorine to PCl₃ is from about 1;

1 to about 3;

1.

2. A method according to claim 1 wherein a carboxylic acid group on an aromatic compound is converted.

3. A method according to claim 1 wherein a carboxylic acid group on an N-heteroaromatic compound is converted.

4. A method according to claim 1 wherein the aromatic compound is ring substituted with at least one sterically compatible group chosen from the group consisting of chloro, fluoro, bromo, nitro, cyano, alkyl, alkoxy, alkylthio, hydroxy, aryl, alkyl substituted aryl, alkoxy substituted aryl, aryloxy or trifluoromethyl with the proviso that when the substituent is alkyl, alkylthio or alkoxy, a strong electron withdrawing group is present on the ring.

5. A method according to claim 1 wherein the N-heteroaromatic compound is ring substituted with at least one sterically compatible group from the group consisting of chloro, fluoro, bromo, nitro, cyano, alkyl, alkoxy, alkylthio, hydroxyl, aryl, alkyl substituted aryl, alkoxy substituted aryl, alkoxy substituted aryl, aryloxy or trifluoromethyl.

6. A method according to claim 1 wherein the compound produced is 3-trichloromethyl pyridine.