C[O:2][C:3]1[CH:21]=[CH:20][C:6]([N:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:5][CH:4]=1.B(Br)(Br)Br.CO.O>C(Cl)Cl>[C:8]1([N:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:6]2[CH:20]=[CH:21][C:3]([OH:2])=[CH:4][CH:5]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1To a solution of 4-methoxy-N,N-diphenylaniline (6.0 g, 21.8 mmol) in DCM (40 mL) was slowly added BBr3 (23 mL, 23 mmol) at about −78° C. The mixture was then stirred overnight under argon while it slowly warmed up to room temperature. To the resulting mixture, methanol (70 mL) was added slowly, then stirred for about 3 hours. The mixture was then poured into water and extracted with DCM (2×200 mL). The organic phases were then combined and washed with brine, dried over Na2SO4, loaded on silica gel, and purified by short plug using hexane/ethyl acetate (9:1 to 8:1). The desired fraction was concentrated and washed with hexanes to give a white solid (Compound 7) (4.59 g, in 81% yield).
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