Benzyl Bromide → 2-(Benzylthio)-5-chloroaniline

HRID 520932Notes

Reaction equation

HRID 520932 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[SH:9].Br[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH2:11]([S:9][C:3]1[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=1[NH2:1])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 120002-Amino-4-chlorobenzenethiol

Product 1

HCID 126182102-(Benzylthio)-5-chloroanilineYield 33.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Following General Procedure A, the title compound (560 mg, 33%) was prepared from 2-amino-4-chlorobenzenethiol (1.08 g, 6.77 mmol), (bromomethyl)benzene (0.8 ml, 6.77 mmol) and K2CO3 (3.18 g, 23.04 mmol) in DMF (20 ml).

Sources & evidence

ORD record
ord-d053fd71c89e4b1f82949bc852ffa452
Source dataset
uspto-grants-2016_05
Patent number
US09328067B2

Reaction notes

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