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

HRID 1631237Notes

Reaction equation

HRID 1631237 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 112.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Following General Procedure A, the title compound (819 mg, 100%) was prepared from 2-amino-4-chlorobenzenethiol (700 mg, 4.39 mmol), (bromomethyl)benzene (560 mg, 2.92 mmol), K2CO3 (2.0 g, 14.62 mmol) in DMF (20 ml).

Sources & evidence

ORD record
ord-b9fd3e5256e94eb5adf2219881fec8e2
Source dataset
uspto-grants-2014_07
Patent number
US08791161B2

Reaction notes

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