3-bromo-4-phenylmethoxyaniline

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

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

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

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 4-amino-1-benzyloxy-2-bromobenzene in 2 mL of dichloromethane at −78 C was added boron trichloride (0.4 mL, 1 M in DCM) dropwise. The reaction was quenched with water at 0 C, concentrated and dried under vacuum to afford 4-amino-2-bromo-1-hydroxybenzene (17 mg, 56% two steps) The reaction was quenched with water at 0 C concentrated dried under vacuum

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

Procedure: To a solution of 1-benzyloxy-2-bromo-4-nitrobenzene (50 mg, 0.16 mmol) in ethanol (5 mL) and H2O (0.5 mL) was added iron (134 mg, 2.43 mmol) and one drop of concentrated HCl. The mixture was refluxed for 6 hrs and filtrated. The filtrate was diluted with ethyl acetate, washed with saturated sodium bicarbonated solution, dried over sodium sulfate and concentrated to afford crude 4-amino-1-benzyloxy-2-bromobenzene. The mixture was refluxed for 6 hrs filtrated The filtrate was diluted with ethyl acetate washed with saturated sodium bicarbonated solution dried over sodium sulfate concentrated