Boron tribromide → 3-(Aminomethyl)-5-chlorophenol

HRID 1715863Notes

Reaction equation

HRID 1715863 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:10]C)[CH:9]=1)[CH2:5][NH2:6].B(Br)(Br)Br>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([OH:10])[CH:9]=1)[CH2:5][NH2:6]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 510637181-(3-Chloro-5-methoxyphenyl)methanamine

Product 1

HCID 510637173-(Aminomethyl)-5-chlorophenolYield 66.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-chloro-5-methoxybenzylamine (4.6 mmol, 0.792 g) in DCM (anhydrous, 20 ml) was cooled to −78° C. and BBr3 (1 M in DCM, 9.43 mmol) was added dropwise. The reaction was allowed to reach room temperature over night with stirring. The reaction was quenched by careful addition of methanol (5 ml), solvents were evaporated under reduced pressure and the residue was purified by means of chromatography (silica, DCM/MeOH/NH3 (30% in water) Sep. 1, 2001 v/v/v) to provide the title compound (0.48 g, 66%) as a white solid. (DMSO, 500 MHz) δ 3.61 (s, 2H), 4.57 (br, 1H), 6.62 (s, 1H), 6.80 (s, 1H) and 6.83 (s, 1H).

Workup

  1. waitto reach room temperature over night
  2. customThe reaction was quenched by careful addition of methanol (5 ml), solvents
  3. customwere evaporated under reduced pressure
  4. customthe residue was purified by means of chromatography (silica, DCM/MeOH/NH3 (30% in water) Sep. 1, 2001 v/v/v)

Sources & evidence

ORD record
ord-fc14f262dd704d089171ec579473abc0
Source dataset
uspto-grants-2010_09
Patent number
US07799947B2

Reaction notes

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