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

HRID 1516618Notes

Reaction equation

HRID 1516618 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

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 870653,4-Dihydroxybenzonitrile

Product 1

HCID 154534514-(Benzyloxy)-3-hydroxybenzonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

3,4-Dihydroxybenzonitrile (5.20 g, 38.5 mmol) and potassium carbonate (5.85 g, 42.4 mmol) were suspended in N,N-dimethylformamide (120 ml), benzyl bromide (4.58 ml) was added, and the mixture was stirred at 50° C. for 3 hours. The solvent was evaporated under reduced pressure, and the residue was diluted with ethyl acetate. The mixture was washed with 1N hydrochloric acid and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel chromatography (hexane:ethyl acetate 8:1-4:1) to give the title compound.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionthe residue was diluted with ethyl acetate
  3. washThe mixture was washed with 1N hydrochloric acid and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel chromatography (hexane:ethyl acetate 8:1-4:1)

Sources & evidence

ORD record
ord-2f141ec79d564846bbba0411b77287e3
Source dataset
uspto-grants-2012_07
Patent number
US08227506B2

Reaction notes

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