Benzyl Bromide → HCID 18973896, compound

HRID 1623633Notes

Reaction equation

HRID 1623633 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([OH:13])=[C:7]([CH:12]=1)[C:8]([O:10][CH3:11])=[O:9])#[N:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CC(C)=O>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:13][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:7]([CH:12]=1)[C:8]([O:10][CH3:11])=[O:9])#[N:2]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 10583428Methyl 5-cyano-2-hydroxybenzoate

Product 1

HCID 18973896HCID 18973896, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
50 °C

Procedure

A suspension of methyl 5-cyano-2-hydroxybenzoate (may be prepared as described in Description 12; 531 mg, 3 mmol), potassium carbonate (1037 mg, 7.50 mmol) and (bromomethyl)benzene (1026 mg, 6.00 mmol) in acetone (60 ml) was stirred at 50° C. overnight. The mixture was cooled and filtered. The filtrate was concentrated. The crude product was purified by silica gel chromatography eluting with hexane:ethyl acetate (10:1) to yield the title compound as a white solid. 480 mg.

Workup

  1. temperatureThe mixture was cooled
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated
  4. customThe crude product was purified by silica gel chromatography
  5. washeluting with hexane:ethyl acetate (10:1)

Sources & evidence

ORD record
ord-a243bfa063384708814b37724f8e456a
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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