Trifluoroacetic acid → 3-Amino-4-chloro-5-(4-hydroxybutan-2-yl)benzonitrile
Reaction equation
[Cl:1][C:2]1[C:7]([CH:8]([CH2:10][CH2:11][OH:12])[CH3:9])=[CH:6][C:5]([C:13]#[N:14])=[CH:4][C:3]=1[NH:15]C(=O)OC(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:15][C:3]1[CH:4]=[C:5]([CH:6]=[C:7]([CH:8]([CH2:10][CH2:11][OH:12])[CH3:9])[C:2]=1[Cl:1])[C:13]#[N:14]Participants
4
Procedure
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.