Benzyl Bromide → 4-Benzyloxy-benzofuran

HRID 479193Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[OH:7][C:8]1[C:13]2[CH:14]=[CH:15][O:16][C:12]=2[CH:11]=[CH:10][CH:9]=1.[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CN(C)C=O>[CH2:17]([O:7][C:8]1[C:13]2[CH:14]=[CH:15][O:16][C:12]=2[CH:11]=[CH:10][CH:9]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

Conditions

Temperature: 2 °C

Procedure

To a suspension of potassium carbonate (2.68 g, 19.4 mmol) in N,N-dimethylformamide (8 ml) was added a solution of 4-hydroxy-benzofuran (2.6 g, 19.4 mmol) in N,N-dimethylformamide (8 ml) at 2° C. under an argon atmosphere (for the preparation of 4-hydroxy-benzofuran see: G. Kneen, P. J. Maddocks, Syn. Commun. 1986, 16, 1635-1640.). After stirring for 50 min at 2° C., benzyl bromide (3.3 ml, 19.4 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 1.5 h at ambient temperature. After adding ice water (20 ml), the solution was extracted two times with diethyl ether. The combined extracts were washed three times with brine and dried over sodium sulfate. Evaporation of the solvent gave a yellow oil which was purified by column chromatography (silica gel, hexane) to give 4.3 g (19.2 mmol, 99%) of the title compound as colorless oil.

Workup

stirringThe suspension was stirred for additional 30 min at 2° C. and for 1.5 h at ambient temperature
extractionthe solution was extracted two times with diethyl ether
washThe combined extracts were washed three 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, hexane)

Sources & evidence

ORD record: ord-976e646fa5a64a4fbf7eb42fc5d01310
Source dataset: uspto-grants-2003_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06642389B2

Reaction notes

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