Benzyl Bromide → 4-(Benzyloxy)-3-hydroxybenzonitrile

HRID 2414408Notes

Reaction equation

[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[C:5]#[N:6].C(=O)([O-])[O-].[K+].[K+].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CN(C)C=O>[CH2:17]([O:10][C:9]1[CH:8]=[CH:7][C:4]([C:5]#[N:6])=[CH:3][C:2]=1[OH:1])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

Conditions

Temperature: 50 °C

Procedure

1.0 g (7.41 mmol) of 3,4-dihydroxybenzonitrile was dissolved in 10 ml of N,N-dimethylformamide. 1.12 g (8.15 mmol) of potassium carbonate and 0.88 ml (7.41 mmol) of benzyl bromide were added to the obtained solution, and they were stirred at 50° C. for 2 hours. After the treatment with ethyl acetate as the extraction solvent in an ordinary manner, the solvent was evaporated, and the obtained residue was purified by the silica gel column chromatography to obtain the title compound.

Workup

customAfter the treatment with ethyl acetate as the extraction solvent in an ordinary manner, the solvent was evaporated
customthe obtained residue was purified by the silica gel column chromatography

Sources & evidence

ORD record: ord-71f3a1b72a474c60803bc40ffaeee47c
Source dataset: uspto-grants-2004_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06812231B2

Reaction notes

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