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

HRID 2215222Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[CH2:7]([C:9]1[CH:10]=[C:11]([OH:15])[CH:12]=[CH:13][CH:14]=1)[CH3:8].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C)C=O>[CH2:7]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:10]=1)[CH3:8]

Participants

Conditions

Temperature: 2 °C

Procedure

To a suspension of potassium carbonate (17 g, 123 mmol) in N,N-dimethylformamide (40 ml) was added a solution of 3-ethyl-phenol (14.8 ml, 123 mmol) in N,N-dimethylformamide (40 ml) at 2° C. under an argon atmosphere. After stirring for 50 min at 2° C., benzyl bromide (14.6 ml, 123 mmol) was added over a period of 15 min at 2° C. The suspension was stirred for additional 30 min at 2° C. and for 12 h at ambient temperature. After adding ice water (250 ml), the solution was extracted two times with diethyl ether. The combined extracts were washed two times with brine and dried over sodium sulfate. Evaporation of the solvent gave a yellow oil which was purified by column chromatography (silica gel, cyclohexane) to yield 24.3 g (114 mmol, 93%) of the title compound as yellow liquid.

Workup

stirringThe suspension was stirred for additional 30 min at 2° C. and for 12 h at ambient temperature
extractionthe solution was extracted two times with diethyl ether
washThe combined extracts were washed two times with brine
dry with materialdried over sodium sulfate
customEvaporation of the solvent
customgave a yellow oil which
customwas purified by column chromatography (silica gel, cyclohexane)

Sources & evidence

ORD record: ord-0554b333fb0f44b0a687c72e46b73287
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07109225B2

Reaction notes

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