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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1409308Generated: October 31, 2026

Ammonia → 4-Amino-2-chloro-6-fluorobenzonitrile

https://huagongshe.com/reaction/1409308

Reaction equation

Participants

RoleNameHCIDCharge
ReactantAmmoniaHCID 222—
ReactantN-methyl-2-pyrrolidoneHCID 13387—
Reactant4-Bromo-3-chloro-5-fluoroanilineHCID 67168370—
ReactantHCID 178418546HCID 178418546—
SolventWaterHCID 962—
Product4-Amino-2-chloro-6-fluorobenzonitrileHCID 5963588370.4%

Reaction Conditions

Temperature160 °C

Reaction Steps

4-Bromo-3-Chloro-5-fluoroaniline (980 mmol, 220 g), copper(I)cyanide (980 mmol, 88 g) and NMP (1000 ml) were added into the reaction flask, heated up to 160° C. and stirred for 3 h to complete the reaction. The reaction mixture was cooled to RT. Water and 25% ammonia solution was added keeping the mixture at RT. The mixture was stirred overnight and the formed precipitate was separated by filtration and flushed with water. The filtered precipitate was dried under vacuum to give 117.7 g of the title compound. 1H-NMR (400 MHz, DMSO-d6): δ 6.41-6.47 (m, 1H), 6.58-6.62 (m, 1H), 6.86 (bs, 2H).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08921378B2
Source datasetuspto-grants-2014_12
ORD IDord-47b86430debb4c03a6dd09ac183176b2
Source noteuspto-grants-2014_12