4-Bromobenzaldehyde → Benzyl 2-(Benzyloxy)-4-(4-Bromobenzylamino)Benzoate

Participants

Reaction Steps

Primary aniline 1 was coupled to 4-bromobenzaldehyde on a 0.7 mmol scale via General Procedure A to furnish 2 (274 mg, 78%): δH (400 MHz, CDCl3) 4.12 (s, 2H, CH2, NHCH2Ph), 4.50 (br s, 1H, NH), 4.92 (s, 2H, CH2, CH2Ph), 5.18 (s, 2H, CH2, CH2Ph), 5.98 (d, J=1.8 Hz, 1H, CH (Ph)), 6.04 (dd, J=8.6 and 1.8 Hz, 1H, CH (Ph)), 7.02 (d, J=8.2 Hz, 2H, 2 CH (Ph)), 7.11-7.34 (m, 12H, 12 CH (Ph)), 7.70 (d, J=8.6 Hz, 1H, CH (Ph)); δC (100 MHz, CDCl3) 46.5, 65.4, 69.9, 97.0, 104.5, 108.2, 120.7, 126.4, 127.2, 127.4, 127.6, 128.0, 128.1, 128.4, 131.4, 133.9, 136.3, 137.0, 152.3, 160.4, 165.3; LRMS (ES+) calcd for [C28H24BrNO3+H] 502.10. found 502.06.

Provenance & Evidence