Boron tribromide → (R)-3-(1-Aminoethyl)phenol

HRID 1020748Notes

Reaction equation

HRID 1020748 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([C@H:9]([NH2:11])[CH3:10])[CH:6]=[CH:7][CH:8]=1.B(Br)(Br)Br>C(Cl)Cl>[NH2:11][C@@H:9]([C:5]1[CH:4]=[C:3]([OH:2])[CH:8]=[CH:7][CH:6]=1)[CH3:10]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 7020759(R)-1-(3-Methoxyphenyl)ethylamine

Product 1

HCID 40427058(R)-3-(1-Aminoethyl)phenolYield 112.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To the solution of (R)-1-(3-Methoxy-phenyl)-ethylamine (0.5 g, 3.31 mmol) in DCM (25 mL) at −78° C. was added 1.0M BBr3 solution in DCM (6.6 mL, 6.62 mmol) dropwise. The solution was warmed to room temperature and the reaction mixture was quenched with methanol (100 mL) and then concentrated in vacuo. This process was repeated until no white fumes were observed upon addition of methanol to afford 3-((R)-1-Amino-ethyl)-phenol as a pale yellow oil (0.51 g) which was used in the next step without further purification.

Workup

  1. customthe reaction mixture was quenched with methanol (100 mL)
  2. concentrationconcentrated in vacuo
  3. additionwere observed upon addition of methanol

Sources & evidence

ORD record
ord-b8976e43bd384dcda29050a7922d5460
Source dataset
uspto-grants-2014_05
Patent number
US08716473B2

Reaction notes

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