Benzyl Bromide → 4-Benzyloxy-benzofuran

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.

1. stirringThe suspension was stirred for additional 30 min at 2° C. and for 1.5 h at ambient temperature
2. extractionthe solution was extracted two times with diethyl ether
3. washThe combined extracts were washed three times with brine
4. dry with materialdried over sodium sulfate
5. customEvaporation of the solvent
6. customgave a yellow oil which
7. customwas purified by column chromatography (silica gel, hexane)

ORD-Eintrag

ord-976e646fa5a64a4fbf7eb42fc5d01310

Quelldatensatz

uspto-grants-2003_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06642389B2