Benzene → 2-Fluoro-N-phenylacetamide

HRID 1065183

Reaction equation

[F:1][C:2]1C=CC=C[C:3]=1[NH2:4].C(OC(=O)C)(=[O:11])C.[CH:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>>[F:1][CH2:2][C:3]([NH:4][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:11]

Participants

Reactant 3

HCID 241Benzene

HCID 7918Acetic Anhydride

HCID 95842-Fluoroaniline

Product 1

HCID 95042-Fluoro-N-phenylacetamide

Procedure

In benzene, 2-fluoroaniline was acetylated with acetic anhydride to obtain 2-fluoroacetanilide. This 2-fluoroacetanilide was held in glacial acetic acid at 43°-52° C. and an equivalent of chlorine gas was introduced, whereby 2-fluoro-4-chloroacetanilide was obtained. This product was deacetylated with hydrochloric acid and neutralized with sodium hydroxide to recover 2-fluoro-4-chloroaniline as an oil boiling at 64°-65° C./0.25 mmHg.

Sources & evidence

ORD record: ord-65735f6d54f24ea4b80fbe379973d5fc
Source dataset: uspto-grants-1982_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04328367

Linked notes

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