4-Bromobenzoic acid → 4-Bromobenzoyl chloride

HRID 1589732Notes

Reaction equation

[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][CH:3]=1.S(Cl)([Cl:13])=O>>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([Cl:13])=[O:7])=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 114644-Bromobenzoic acid

HCID 24386Thionyl Chloride

Product 1

HCID 685154-Bromobenzoyl chloride

Procedure

Compound [H], 4-bromobenzoic acid is chlorinated with thionyl chloride to yield compound [I], 4-bromobenzoic acid chloride. Compound [I] is reacted with aqueous ammonia to yield compound [J] 4-bromobenzoic acid amide. Compound [J] is dehydrated with thionyl chloride to yield compound [K], a 4-bromobenzonitrile. Compound [K] is reacted with gaseous hydrogen chloride in anhydrous ethanol to yield compound [L], 4-bromobenzimidate hydrogen chloride. In ethanol, compound [L] is reacted with gaseous ammonia to yield compound [M], 4-bromobenzamidine hydrogen chloride.

Sources & evidence

ORD record: ord-7fe61b042272470eb48e22a79bbc4afc
Source dataset: uspto-grants-1993_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05200110

Reaction notes

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