Benzyl Bromide → 2,2-Difluoro-1-benzyloxy-4-pentene

HRID 568976Notes

Reaction equation

HRID 568976 reaction equation
[F:1][C:2]([F:7])([CH2:4][CH:5]=[CH2:6])[CH3:3].[CH2:8](Br)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.CC(C)([O-:19])C.[K+]>O1CCCC1>[F:1][C:2]([F:7])([CH2:4][CH:5]=[CH2:6])[CH2:3][O:19][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 201494832,2-Difluoro 4-penteneHCID 23665647Potassium tert-butoxide

Product 1

HCID 201494522,2-Difluoro-1-benzyloxy-4-pentene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 2,2-difluoro 4-pentene (9.8 g, 80 mmoles) and benzyl bromide (13.7 g, 80 mmoles) in dry tetrahydrofuran (100 ml), potassium t-butoxide (9.5 g, 85 mmoles) is added in portions over a period of 1 hour. The reaction mixture is kept overnight at room temperature, concentrated under reduced pressure, hydrolyzed with 1N HCl (pH approximately 2) and diluted with water and ether. Usual work-up gives 2,2-difluoro-1-benzyloxy-4-pentene as a colorless oil (16.8 g, , 99%, RF: 0.2, ethyl acetate/petroleum ether: 2/98).

Workup

  1. additionis added in portions over a period of 1 hour
  2. concentrationconcentrated under reduced pressure, hydrolyzed with 1N HCl (pH approximately 2)
  3. additiondiluted with water and ether

Sources & evidence

ORD record
ord-645262eac8174bdf81772cc995cfc5fe
Source dataset
uspto-grants-1988_03
Patent number
US04730006

Reaction notes

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