Boron tribromide → 2-(3-Amino-3-methylbutyl)phenol

HRID 1164900Notes

Reaction equation

HRID 1164900 reaction equation
[NH2:1][C:2]([CH3:14])([CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[O:12]C)[CH3:3].B(Br)(Br)Br>C(Cl)Cl>[NH2:1][C:2]([CH3:14])([CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[OH:12])[CH3:3]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 183496784-(2-Methoxyphenyl)-2-methylbutan-2-amine

Product 1

HCID 198636832-(3-Amino-3-methylbutyl)phenol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a cold (0° C.) solution of 986 mg (5.1 mmol) of 2-amino-2-methyl-4-(2-methoxyphenyl)butane in 20 ml of dry methylene chloride, a solution of 2.5 ml of a 1M BBr3 solution in 10 ml of methylene chloride is slowly added. The reaction mixture is stirred at 0° C. for two hours and then at room temperature for 3 hours. The reaction is quenched with methanol and concentrated. Pure product may be obtained by chromatography on silica gel.

Workup

  1. waitat room temperature for 3 hours
  2. customThe reaction is quenched with methanol
  3. concentrationconcentrated
  4. customPure product may be obtained by chromatography on silica gel

Sources & evidence

ORD record
ord-c956abd3e0b54d23b5c05a3624702051
Source dataset
uspto-grants-1990_03
Patent number
US04906645

Reaction notes

Loading…