Trifluoroacetic acid → 3-Pyridylthio-2-phenylbenzoic acid

HRID 2121212Notes

Reaction equation

HRID 2121212 reaction equation
C([O:5][C:6](=[O:26])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([S:13][C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)[C:8]=1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)(C)(C)C.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>ClCCl>[N:16]1[CH:17]=[CH:18][CH:19]=[C:14]([S:13][C:9]2[C:8]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[C:7]([CH:12]=[CH:11][CH:10]=2)[C:6]([OH:26])=[O:5])[CH:15]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 538048533-Pyridylthio-2-phenylbenzoic acid tert-butyl ester

Product 1

HCID 234363563-Pyridylthio-2-phenylbenzoic acidYield 101.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 0° C. solution in dichloromethane (1 mL) of 3-pyridylthio-2-phenylbenzoic acid tert-butyl ester (245 mg, 0.67 mmol), prepared as in Example 241 A, and triethylsilane (390 mg, 3.4 mmol) was added trifluoroacetic acid (1.53 g, 13.4 mmol) and the reaction mixture was warmed to ambient temperature and stirred for 18 hours. The reaction mixture was concentrated and azeotroped with toluene (3×) to give 3-pyridylthio-2-phenylbenzoic acid (209 mg) as a translucent film which was used without further purification.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customazeotroped with toluene (3×)

Sources & evidence

ORD record
ord-3b720c296f1d4b178048e8ac1b95d411
Source dataset
uspto-grants-2004_02
Patent number
US06693123B2

Reaction notes

Loading…