1-Bromo-2-Chloroethane → 1-Chloro-4-((2-chloroethyl)thio)benzene

HRID 2413330Notes

Reaction equation

HRID 2413330 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][Si](C)(C)C)=[CH:4][CH:3]=1.Br[CH2:14][CH2:15][Cl:16]>CN(C)P(=O)(N(C)C)N(C)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:14][CH2:15][Cl:16])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 78491-Bromo-2-ChloroethaneHCID 111068011-Chloro-4-[(trimethylsilyl)thio]benzene

Product 1

HCID 843931-Chloro-4-((2-chloroethyl)thio)benzeneYield 85.7%

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture consisting of 12.21 g (56.5 mmoles) of 4-chlorophenylthio(trimethyl)silane, 20 ml of hexamethylphosphoric triamide and 18.7 ml (226 mmoles) of 1-bromo-2-chloroethane was heated at 60° C. and it was established that the conversion was complete after 10 minutes. After treating the reaction mixture as described in Example 3, there were obtained 10.03 g (85.7% yield) of 2-chloroethyl 4-chlorophenyl sulfide boiling at 105°-109° C./1.0 mm Hg and melting at 28°-29° C. The residue of the distillation contained 1,2-bis(4-chlorophenylthio)ethane as a by-product which after crystallization from methanol melted at 87°-88° C.

Workup

  1. additionAfter treating the reaction mixture

Sources & evidence

ORD record
ord-ada9ab912b264928bee19e8fb64f8b4f
Source dataset
uspto-grants-1985_01
Patent number
US04496720

Reaction notes

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