Carbon tetrabromide → ((4-Bromobutoxy)methyl)benzene

HRID 1838894Notes

Reaction equation

HRID 1838894 reaction equation
Br[C:2]([Br:5])(Br)Br.[CH2:6]([O:13][CH2:14][CH2:15][CH2:16]CO)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[CH2:6]([O:13][CH2:14][CH2:15][CH2:16][CH2:2][Br:5])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 5622124-Benzyloxy-1-butanol

Product 1

HCID 4422181((4-Bromobutoxy)methyl)benzeneYield 93.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-15 °C

Procedure

239 g of tetrabromomethane are added in portions to the solution of 105 g of 4-benzyloxybutan-1-ol and 191 g of triphenylphosphine in 1 l of methylene chloride cooled to −15° C. and the mixture is stirred at 0° C. for 1 h after addition is complete. After the reaction mixture has been concentrated in vacuo, purification is carried out by chromatography on silica gel using a hexane-ethyl acetate gradient. 133 g of 4-benzyloxy-1-bromobutane are obtained as an oil.

Workup

  1. additionafter addition
  2. concentrationAfter the reaction mixture has been concentrated in vacuo, purification

Sources & evidence

ORD record
ord-21a77f106baa4cf69f5885c5ae9f1533
Source dataset
uspto-grants-2004_01
Patent number
US06677324B1

Reaction notes

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