Hydrochloric Acid → 4-Chloro-2-fluoroaniline

HRID 1076919Notes

Reaction equation

[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([NH:6]C(=O)C)=[C:4]([F:12])[CH:3]=1.Cl>>[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([NH2:6])=[C:4]([F:12])[CH:3]=1

Participants

Reactant 2

HCID 313Hydrochloric Acid

HCID 8531744'-Chloro-2'-fluoroacetanilide

Product 1

HCID 938984-Chloro-2-fluoroaniline

Procedure

4'-Chloro-2'-fluoroacetanilide is refluxed in a mixture of a lower alcohol (50%) (e.g. ethanol) and concentrated hydrochloric acid (50%) for several hours (e.g. 5 or more) at 70°-90°C and atmospheric pressure. The solvent mixture is removed at a reduced pressure of 100 to 300 mm Hg. and 20°-50°C to leave a residue of the hydrochloride salt of 4-chloro-2-fluoroaniline.

Workup

customThe solvent mixture is removed at a reduced pressure of 100 to 300 mm Hg

Sources & evidence

ORD record: ord-e3701b43a84243938678cfd07721f87c
Source dataset: uspto-grants-1976_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03958976

Reaction notes

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