Benzyl Bromide → 3-Benzyloxy-5-hydroxybenzonitrile

HRID 2387660Notes

Reaction equation

C(=O)([O-])[O-].[Cs+].[Cs+].[OH:7][C:8]1[CH:9]=[C:10]([CH:13]=[C:14]([OH:16])[CH:15]=1)[C:11]#[N:12].[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[CH:9]=[C:10]([CH:13]=[C:14]([OH:16])[CH:15]=1)[C:11]#[N:12])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Caesium carbonate (2.41 g, 7.4 mmol) was added to a solution of 3,5-dihydroxy benzonitrile (1.0 g, 7.4 mmol) in dimethylformamide (5 ml) at room temperature and the mixture stirred for 10 minutes. Benzyl bromide (0.880 ml, 7.4 mmol) was added dropwise and the mixture heated at 80° C. for 30 minutes. The solvent was removed in vacuo, the residue treated with water (10 ml), acidified with aqueous hydrochloric acid (2M) and extracted with ethyl acetate (3×25 ml). The combined organic layers were washed with water (2×10 ml), brine (10 ml), dried over sodium sulphate and concentrated in vacuo. The residue was purified by column chromatography, eluting with ethyl acetate/pentane (20:80 to 50:50) to afford the title compound as a white solid in 26% yield, 445 mg.

Workup

customThe solvent was removed in vacuo
additionthe residue treated with water (10 ml)
extractionextracted with ethyl acetate (3×25 ml)
washThe combined organic layers were washed with water (2×10 ml), brine (10 ml)
dry with materialdried over sodium sulphate
concentrationconcentrated in vacuo
customThe residue was purified by column chromatography
washeluting with ethyl acetate/pentane (20:80 to 50:50)

Sources & evidence

ORD record: ord-b78875d8760244ed83ca5a69793cf8ef
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08268881B2

Reaction notes

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