Water → HCID 66611357, compound

HRID 2204681Notes

Reaction equation

HRID 2204681 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.[Br:15][C:16]1[C:21]([CH3:22])=[CH:20][C:19]([C:23](=[O:25])[CH3:24])=[C:18]([OH:26])[CH:17]=1.O>CN(C)C=O.C(OCC)(=O)C>[Br:15][C:16]1[C:21]([CH3:22])=[CH:20][C:19]([C:23](=[O:25])[CH3:24])=[C:18]([O:26][CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:17]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 425530931-(4-Bromo-2-hydroxy-5-methylphenyl)ethan-1-one

Product 1

HCID 66611357HCID 66611357, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Potassium carbonate (1.45 g, 10.48 mmol) and benzyl bromide (0.65 ml, 5.50 mmol) were added to a solution of 1-(4-bromo-2-hydroxy-5-methylphenyl)ethanone (may be prepared as described in Description 10; 1.2 g, 5.24 mmol) in N,N-dimethylformamide (10 ml). The mixture was stirred at room temperature overnight. Water (20 ml) and ethyl acetate (30 ml) were added and the organic layer was separated, washed with water (2×20 ml), dried (MgSO4) and the solvent removed in vacuo. Purification by column chromatography (5-10% ethyl acetate/hexane) yielded the title compound. 607 mg.

Workup

  1. customthe organic layer was separated
  2. washwashed with water (2×20 ml)
  3. dry with materialdried (MgSO4)
  4. customthe solvent removed in vacuo
  5. customPurification by column chromatography (5-10% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-c3740497696c4304b090206b3cdbc141
Source dataset
uspto-grants-2016_06
Patent number
US09365551B2

Reaction notes

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