Carbon tetrabromide → 4-(Bromomethyl)phenyl acetate

HRID 552049Notes

Reaction equation

HRID 552049 reaction equation
[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11]O)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].C(Br)(Br)(Br)[Br:14].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][Br:14])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 959064-Acetoxybenzyl alcohol

Product 1

HCID 109987714-(Bromomethyl)phenyl acetateYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the solution of 4-hydroxymethylphenol acetate (2.50 g, 15.0 mmol) and carbon tetrabromide (5.97 g, 18.0 mmol) in 40 ml of methylene chloride was added triphenylphosphine (4.73 g, 180 mmol) under nitrogen. The resultant mixture was stirred for 3 hours. The product was purified by flash chromatography using heptane/ethyl acetate (90/10-80/20) as eluent in a yield of 79%.

Workup

  1. customThe product was purified by flash chromatography

Sources & evidence

ORD record
ord-e57dfc24af984272a18d47a6c4921a3a
Source dataset
uspto-grants-2011_05
Patent number
US07951550B2

Reaction notes

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