Boron tribromide → 2-(2-bromoethyl)phenol

HRID 1870974Notes

Reaction equation

HRID 1870974 reaction equation
C[O:2][C:3]1[CH:11]=[CH:10][CH:9]=[CH:8][C:4]=1[CH2:5][CH2:6][Br:7].B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:11]=[CH:10][CH:9]=[CH:8][C:4]=1[CH2:5][CH2:6][Br:7]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 5781992-Methoxyphenethyl bromide

Product 1

HCID 139806682-(2-bromoethyl)phenol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-methoxyphenethyl bromide (1.07 g, 4.98 mmol) in 5 ml of CH2Cl2 was added BBr3 (9.5 ml, 1.0 M in CH2Cl2) at -78° C. and it was allowed to warm to rt over 1.5 h. The reaction mixture was poured into CH2Cl2 and was washed with brine, dried to afford 2-hydroxy phenethyl bromide (quantitative).

Workup

  1. washwas washed with brine
  2. customdried

Sources & evidence

ORD record
ord-f8675d76a196499e902690957764b345
Source dataset
uspto-grants-2000_08
Patent number
US06100293

Reaction notes

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