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

HRID 646220Notes

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

Reactant 3

HCID 7498Benzyl Bromide

HCID 11430Potassium Carbonate

HCID 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%). 1HNMR (400 MHz, CDCl3): δ (ppm) 3.05 (s, 1H), 5.05 (s, 2H), 6.98 (d, 1H) 7.00-7.50 (m, 8H).

Workup

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

Sources & evidence

ORD record: ord-fbd6274430d94483831aa7e4e24cbe05
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07705030B2

Reaction notes

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