Thiophenol → 4-(Phenylthio)benzoic acid

HRID 440753Notes

Reaction equation

HRID 440753 reaction equation
[SH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].Br[C:15]1[CH:23]=[CH:22][C:18]([C:19]([OH:21])=[O:20])=[CH:17][CH:16]=1>>[C:2]1([S:1][C:15]2[CH:23]=[CH:22][C:18]([C:19]([OH:21])=[O:20])=[CH:17][CH:16]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 7969ThiophenolHCID 114644-Bromobenzoic acidHCID 23665647Potassium tert-butoxide

Product 1

HCID 2385984-(Phenylthio)benzoic acidYield 95.7%

Procedure

The conditions to prepare Reference Example 32 c1384847 are used with 6.0 g of mercaptobenzene, 12.22 g of potassium t-butoxide and 13.15 g of 4-bromobenzoic acid to give 12.0 g of the desired product as a solid, m.p. 101°-103° C.; M+H=231.

Sources & evidence

ORD record
ord-8247575731d84373956f6660ada1c1b4
Source dataset
uspto-grants-1996_05
Patent number
US05521173

Reaction notes

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