Phenol → HCID 66779142, compound

HRID 2091137Notes

Reaction equation

HRID 2091137 reaction equation
Br[CH2:2][C:3]([C:5]1[O:6][C:7]2[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=2[C:9]=1[CH3:10])=[O:4].[C:15]1([OH:21])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].[Cl-].[NH4+]>CN(C)C=O>[CH3:10][C:9]1[C:8]2[CH:11]=[CH:12][CH:13]=[CH:14][C:7]=2[O:6][C:5]=1[C:3](=[O:4])[CH2:2][O:21][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 996PhenolHCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 38482132-Bromo-1-(3-methyl-1-benzofuran-2-yl)ethan-1-one

Product 1

HCID 66779142HCID 66779142, compoundYield 66.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 2-bromo-1-(3-methyl-1-benzofuran-2-yl)ethanone (1.00 g), phenol (446 mg) and N,N-dimethylformamide (20 mL) was added potassium carbonate (655 mg), and the mixture was stirred overnight at room temperature. Saturated aqueous ammonium chloride solution was added to quench the reaction, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (10% ethyl acetate/hexane) to give the title object compound (697 mg, 66%) as a yellow solid.

Workup

  1. customto quench
  2. customthe reaction
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (10% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-c5f1201b16c64da08c07cb39b1c6dd7e
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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