Benzyl Bromide → 1-(Benzyloxy)-3-ethynylbenzene

HRID 2220442Notes

Reaction equation

HRID 2220442 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:8]#[CH:9])[CH:5]=[CH:6][CH:7]=1.[CH2:10](Br)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C([O-])([O-])=O.[K+].[K+]>>[CH2:10]([O:1][C:2]1[CH:3]=[C:4]([C:8]#[CH:9])[CH:5]=[CH:6][CH:7]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 139144m-Ethynylphenol

Product 1

HCID 194222281-(Benzyloxy)-3-ethynylbenzeneYield 609%

Procedure

A mixture of 3-hydroxy-1-ethynylbenzene (4.36 g, 37 mmol), benzylbromide (6.95 g, 4.1 mmol) and K2CO3 (10.2 g, 7.4 mmol) in acetanitrile (50 ml) is stirred at room temperature for 24 hr. The insoluble material is removed by filtration and filtrate is concentrated. The crude material is purified by flash chromatography (silica gel, hexane/EtOAc: 95/5) to afford the title compound as a clear oil 5.2 g (68%).

Workup

  1. customThe insoluble material is removed by filtration and filtrate
  2. concentrationis concentrated
  3. customThe crude material is purified by flash chromatography (silica gel, hexane/EtOAc: 95/5)

Sources & evidence

ORD record
ord-c6d47252ddec4220abfeb9f973863370
Source dataset
uspto-grants-2008_08
Patent number
US07417047B2

Reaction notes

Loading…