2-(4-amino-3-bromophenyl)ethanol

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-(4-amino-phenyl)-ethanol (5.10 g, 37.2 mmol) in 37 mL of DMF was added NBS (6.60 g, 37.1 mmol) and the mixture stirred overnight at RT. The reaction was diluted with 100 mL of water and extracted with EtOAc (3×100 mL). The organic layer was washed with brine (200 mL) and dried over Na2SO4. The title compound was purified by silica gel flash chromatography eluting with 50% EtOAc/hexanes to give 5.10 g (64%) of a white solid. Mass spectrum (ESI, m/z): Calcd. for C8H10BrNO, 216.0 (M+H), found 216.1. extracted with EtOAc (3×100 mL) The organic layer was washed with brine (200 mL) dried over Na2SO4 The title compound was purified by silica gel flash chromatography eluting with 50% EtOAc/hexanes

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 4-aminophenyl ethanol (34 g, 0.25 mol) and NBS (35 g, 0.20 mol) in DMF (660 mL) was stirred at RT overnight. Then the mixture was diluted with ethyl acetate (2 L), washed with water (300 mL×4), dried over Na2SO4, concentrated in vacuo to give the crude product 2-(4-Amino-3-bromophenyl)ethanol. 1H NMR (400 MHz, CDCl3) δ 7.26 (d, J=1.6 Hz, 1H), 6.93 (d, J=1.6 Hz, 1H), 6.70 (s, 1H), 4.44 (br, 1H), 3.76 (t, J=6.4 Hz, 2H), 2.71 (t, J=6.4 Hz, 2H). washed with water (300 mL×4) dried over Na2SO4 concentrated in vacuo