Water → Benzenamine, 4-chloro-2-fluoro-5-(2-propynyloxy)-

HRID 2295940Notes

Reaction equation

[Cl:1][C:2]1[C:7]([O:8][CH2:9][C:10]#[CH:11])=[CH:6][C:5]([N+:12]([O-])=O)=[C:4]([F:15])[CH:3]=1.O>C(O)(=O)C.[Fe]>[Cl:1][C:2]1[C:7]([O:8][CH2:9][C:10]#[CH:11])=[CH:6][C:5]([NH2:12])=[C:4]([F:15])[CH:3]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A suspension of electrolytic iron powder (3.5 g) in a 5% aqueous acetic acid solution was heated to 90° C., and a solution of 4-chloro-2-fluoro-5-(2-propynyloxy)nitrobenzene (5.7 g) in acetic acid (40 ml) was dropwise added thereto at the same temperature. The resultant mixture was stirred for at 90°-105° C. for 1 hour and allowed to cool to room temperature. Water (200 ml) was added thereto. Insoluble materials were filtered off, and the filtrate was neutralized, followed by extraction with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and concentrated. The residue was washed with petroleum ether and carbon tetrachloride to give 3.6 g of 4-chloro-2-fluoro-5-(2-propynyloxy)aniline. M.P. 61.0°-61.5° C.

Workup

temperatureto cool to room temperature
filtrationInsoluble materials were filtered off
extractionfollowed by extraction with ethyl acetate
dry with materialThe extract was dried over anhydrous magnesium sulfate
concentrationconcentrated
washThe residue was washed with petroleum ether and carbon tetrachloride

Sources & evidence

ORD record: ord-350b6e405fe245e584c718765b832daf
Source dataset: uspto-grants-1984_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04427438

Reaction notes

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