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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 921852Generated: October 30, 2026

Trifluoroacetic acid → 3-Amino-4-chloro-5-(4-hydroxybutan-2-yl)benzonitrile

https://huagongshe.com/reaction/921852

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTrifluoroacetic acidHCID 6422—
ReactantTert-butyl (2-chloro-5-cyano-3-(4-hydroxybutan-2-yl)phenyl)carbamateHCID 131734941—
SolventDichloromethaneHCID 6344—
Product3-Amino-4-chloro-5-(4-hydroxybutan-2-yl)benzonitrileHCID 89922413127.4%

Reaction Steps

Tert-butyl (2-chloro-5-cyano-3-(4-hydroxybutan-2-yl)phenyl)carbamate (184 mg, 0.566 mmol) was taken up in DCM (6 mL) and TFA (1.746 mL, 22.66 mmol) was added. The reaction was stirred at room temperature for 1 h. LCMS indicates a mixture of the alcohol and the TFA ester. The solvent was removed in vacuo and the material dissolved in 2N NH3 in MeOH. The solution was stirred at room temperature for 10 min and the solvent removed in vacuo. 3-amino-4-chloro-5-(4-hydroxybutan-2-yl)benzonitrile (162 mg) was obtained. The crude material was taken forward without purification.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09273057B2
Source datasetuspto-grants-2016_03
ORD IDord-69bc3f9d5939457d81890c815bc5dce1
Source noteuspto-grants-2016_03