Benzyl Bromide → HCID 12159480, compound

HRID 657841Notes

Reaction equation

HRID 657841 reaction equation
C(=O)([O-])[O-].[K+].[K+].[Cl:7][C:8]1[CH:15]=[C:14]([OH:16])[CH:13]=[CH:12][C:9]=1[C:10]#[N:11].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(#N)C>[CH2:17]([O:16][C:14]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[C:8]([Cl:7])[CH:15]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 5927972-Chloro-4-hydroxybenzonitrile

Product 1

HCID 12159480HCID 12159480, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Potassium carbonate (66.3 g, 480 mmol) was added to a mixture of 2-chloro-4-hydroxybenzonitrile (25 g, 160 mmol) and benzyl bromide (19.3 mL, 161 mmol) in acetonitrile (300 mL) and the mixture was stirred for 18 hours at room temperature. The reaction mixture was then filtered and the filtrate was concentrated in vacuo. Trituration of the residue with heptanes afforded the title compound as an off-white solid in 99% yield, 38.65 g.

Workup

  1. filtrationThe reaction mixture was then filtered
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-6b8275c7cdcf48f8853e986c610bd32a
Source dataset
uspto-grants-2011_12
Patent number
US08076356B2

Reaction notes

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