Triphenylphosphine → 1-(Benzyloxy)-4-(bromomethyl)benzene

HRID 842823

Reaction equation

HRID 842823 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13]O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:17]N1C(=O)CCC1=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13][Br:17])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 70043(4-(Benzyloxy)phenyl)methanol

Product 1

HCID 104927561-(Benzyloxy)-4-(bromomethyl)benzeneYield 92.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 4-benzyloxybenzyl alcohol (8.1 g, 37.8 mmol) in dichloromethane (160 mL) was added N-bromosuccinimide (7.4 g, 41.6 mmol) followed by portionwise addition of triphenylphosphine (10.9 g, 41.6 mmol). The reaction mixture was stirred at room temperature for 5 minutes, and was then concentrated in vacuo. Purification by flash chromatography, eluting with 80:20 hexanes/ethyl acetate, provided 9.7 g (92%) of 1 as a white solid.

Workup

  1. concentrationwas then concentrated in vacuo
  2. customPurification by flash chromatography
  3. washeluting with 80:20 hexanes/ethyl acetate

Sources & evidence

ORD record
ord-f39884177c904d33a35be9aaa071ab23
Source dataset
uspto-grants-2002_04
Patent number
US06376524B1

Linked notes

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