Carbon tetrabromide → 4-(Bromomethyl)phenyl acetate

HRID 446199

Reaction equation

HRID 446199 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-fc733c6b446f4213ba233c61ef64153c
Source dataset
uspto-grants-2013_07
Patent number
US08476450B2

Linked notes

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