2,4,4,6-Tetrabromocyclohexa-2,5-dienone → 4-Bromo-2-methoxy-3-(trifluoromethyl)aniline
Reaction equation
[CH3:1][O:2][C:3]1[C:9]([C:10]([F:13])([F:12])[F:11])=[CH:8][CH:7]=[CH:6][C:4]=1[NH2:5].[Br:14]C1C(=O)C(Br)=CC(Br)(Br)C=1>C(Cl)Cl>[Br:14][C:8]1[CH:7]=[CH:6][C:4]([NH2:5])=[C:3]([O:2][CH3:1])[C:9]=1[C:10]([F:11])([F:12])[F:13]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of compound 17C (200 mg, 1.05 mmol) in CH2Cl2 (2 mL) cooled to −20° C. was added dropwise a solution of 2,4,4,6-tetrabromo-2,5-cyclohexadienone (429 mg, 1.05 mmol) in CH2Cl2 (2 mL). After the addition, the reaction was stirred at rt overnight, then additional amount of 2,4,4,6-tetrabromo-2,5-cyclohexadienone (429 mg, 1.05 mmol) was added. The reaction was continued for 2 more days, then concentrated under reduced pressure. The residue was chromatographed (silica gel) eluting with 10%-20% EtOAc/hexane to yield the title compound (47mg, 16% yield).