Benzyl Bromide → HCID 12418340, compound

HRID 1582616Notes

Reaction equation

HRID 1582616 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7](Br)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[Cl:15][C:16]1[CH:17]=[CH:18][C:19]([OH:25])=[C:20]([C:22](=[O:24])[CH3:23])[CH:21]=1>CN(C)C=O>[CH2:7]([O:25][C:19]1[CH:18]=[CH:17][C:16]([Cl:15])=[CH:21][C:20]=1[C:22](=[O:24])[CH3:23])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 740613-Chloro-6-hydroxyacetophenone2×

Product 1

HCID 12418340HCID 12418340, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Potassium carbonate powder (2.9 g, 21.0 mmol) and benzyl bromide (2.3 g, 18.2 mmol) was added to a solution of 1-(5-chloro-2-hydroxyphenyl)-1-ethanone [compound (8-1)] (3.0 g, 17.6 mmol) in dimethylformamide (50 mL), and the mixture was stirred for 3 hours at 60° C. After cooling, ice-water was added to the resultant mixture, followed by extraction with ethyl acetate. The mixture was washed with aqueous sodium hydroxide (5%) and water, and dried over magnesium sulfate. The solvent was removed under reduced pressure, to thereby yield compound (9-1) as a colorless oily product (4.6 g, yield: 99.9%).

Workup

  1. temperatureAfter cooling
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe mixture was washed with aqueous sodium hydroxide (5%) and water
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-8febc681ff9e4b418a9e969367abe6ca
Source dataset
uspto-grants-2004_05
Patent number
US06737434B2

Reaction notes

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