Propargyl bromide → 1-Bromo-4-fluoro-2-[(prop-2-yn-1-yl)oxy]benzene

HRID 618719Notes

Reaction equation

HRID 618719 reaction equation
[CH2:1](Br)[C:2]#[CH:3].[Br:5][C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][C:7]=1[OH:13].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Br:5][C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][C:7]=1[O:13][CH2:3][C:2]#[CH:1]

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 27246002-Bromo-5-fluorophenol

Product 1

HCID 224828471-Bromo-4-fluoro-2-[(prop-2-yn-1-yl)oxy]benzeneYield 97.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 42.95 g (0.36 mol) of propargyl bromide in 30 ml of dimethylformamide was added dropwise to a suspension of 50 g (0.26 mol) of 2-bromo-5-fluoro-phenol and 55 g of potassium carbonate in 300 ml of dimethylformamide and the mixture was subsequently stirred at room temperature for two hours. The mixture was poured on to 1500 ml of ice-water and extracted three times with 600 ml of dichloromethane each time. After drying over sodium sulfate concentration was carried out in a vacuum. The crude product obtained was purified by column chromatography on silica gel (dichloromethane/hexane 1:1). 58 g (97%) of 1-bromo-4-fluoro-2-prop-2-ynyloxy-benzene were obtained as a pale yellow oil.

Workup

  1. extractionextracted three times with 600 ml of dichloromethane each time
  2. dry with materialAfter drying over sodium sulfate concentration
  3. customThe crude product obtained
  4. customwas purified by column chromatography on silica gel (dichloromethane/hexane 1:1)

Sources & evidence

ORD record
ord-e06e1d0fcf2b4010b0fc694fbb639c2d
Source dataset
uspto-grants-1999_09
Patent number
US05955495

Reaction notes

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