Thionyl Chloride → Benzonitrile, 4-bromo-

HRID 1589745Notes

Reaction equation

[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=O)=[CH:4][CH:3]=1.O=S(Cl)Cl>>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]#[N:8])=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 24386Thionyl Chloride

HCID 696834-Bromobenzamide

Product 1

HCID 12162Benzonitrile, 4-bromo-Yield 84.1%

Procedure

88 g (0.44 mol) of 4-bromobenzoic acid amide and 320 cm3 (4.4 mol) of SOCl2 were refluxed on a warm water bath for 10 hours. The excess SOCl2 was distilled off on warm water bath under reduced pressure using an aspirator and the residue was reorystallized from methanol to yield 67 g (0.37 mol) of 4-bromobenzonitrile.

Workup

distillationThe excess SOCl2 was distilled off
temperatureon warm water bath under reduced pressure

Sources & evidence

ORD record: ord-f13b94d871d144209b6c948aa0ddd092
Source dataset: uspto-grants-1993_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05200110

Reaction notes

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