Carbon tetrabromide → 1-(Benzyloxy)-4-(2-bromoethyl)benzene

HRID 1488336Notes

Reaction equation

HRID 1488336 reaction equation
[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:12]([CH2:13][CH2:14]O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Br)(Br)(Br)[Br:19].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CCOCC>[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:12]([CH2:13][CH2:14][Br:19])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 3017260p-(Benzyloxy)phenethyl alcohol

Product 1

HCID 166388271-(Benzyloxy)-4-(2-bromoethyl)benzene

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 4-benzyloxyphenethyl alcohol (8.29 g) and carbon tetrabromide (24.1 g) in ether (150 ml) is portionwise added triphenylphosphine (19.0 g) and the resulting mixture stirred for about 3 hours. The supernatent is decanted, the solid washed with ether and the combined organic solution concentrated in vacuo. The crude product is purified by passing it through a silica plug to give 4-benzyloxyphenethyl bromide.

Workup

  1. customThe supernatent is decanted
  2. washthe solid washed with ether
  3. concentrationthe combined organic solution concentrated in vacuo
  4. customThe crude product is purified

Sources & evidence

ORD record
ord-c76af088952046e48c1276268c711092
Source dataset
uspto-grants-1997_10
Patent number
US05674482

Reaction notes

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