4-Hydroxybiphenyl → 4-Phenylbenzene-1-thiol

HRID 650314Notes

Reaction equation

HRID 650314 reaction equation
O[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.CN(C)C(Cl)=[S:17]>>[SH:17][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 71034-HydroxybiphenylHCID 27871Dimethylthiocarbamoyl chloride

Product 1

HCID 27604144-Phenylbenzene-1-thiolYield 39%

Procedure

The reaction of p-hydroxybiphenyl with dimethylthiocarbamoyl chloride followed by Newman-Kwart rearrangement and finally hydrolysis (see J. Het. Chem. 15, 281 (1978) and WO 96/25 936) affords 4-mercaptobiphenyl only in a yield of 39%.

Workup

  1. customfollowed by Newman-Kwart rearrangement and finally hydrolysis (see J. Het. Chem. 15, 281 (1978) and WO 96/25 936)

Sources & evidence

ORD record
ord-449312bae85e473ea90313a75110cecd
Source dataset
uspto-grants-2001_08
Patent number
US06271415B1

Reaction notes

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