Thiophenol → HCID 21794508, compound

HRID 2309826Notes

Reaction equation

HRID 2309826 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([OH:7])=[O:6].[C:12]1([SH:18])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>N1C2C(=CC=CC=2)C=CC=1>[C:12]1([S:18][C:2]2[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=2[CH3:11])[C:5]([OH:7])=[O:6])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 7969ThiophenolHCID 821303-Bromo-4-methylbenzoic acid

Product 1

HCID 21794508HCID 21794508, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 7047QuinolineSolvent

Procedure

Reaction of 3-bromo-4-methylbenzoic acid 1 with thiophenol and cuprous oxide in quinoline at 180° C produces 3-phenylthio-4-methylbenzoic acid 5 in 95-96% yield. Generation of the dianion of 5 is ccomplished by sequential treatment with sodium ydride and then lithium diisopropylamide in a olvent mixture of tetrahydrofuran and 1,3-dimethylmidazolidinone at -20° C. Carboxylation at -15° with carbon dioxide at a pressure of one atmosphere produces the diacid 6 in 90% yield.

Sources & evidence

ORD record
ord-ce31244118d34aefa889af1bd53c9d84
Source dataset
uspto-grants-1987_09
Patent number
US04697037

Reaction notes

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