Water → 1-(5-Fluoro-3-methyl-1-benzofuran-2-yl)-2-methylpropan-1-one

HRID 2091403Notes

Reaction equation

HRID 2091403 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH:8]=[C:7]([CH3:10])[C:6]=2[CH:11]=1.[C:12](Cl)(=[O:16])[CH:13]([CH3:15])[CH3:14].[Cl-].[Al+3].[Cl-].[Cl-].O>[N+](C)([O-])=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:12](=[O:16])[CH:13]([CH3:15])[CH3:14])=[C:7]([CH3:10])[C:6]=2[CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 62325Isobutyryl chlorideHCID 6451240Aluminum(III) ChlorideHCID 116798475-Fluoro-3-methylbenzofuran

Product 1

HCID 667778481-(5-Fluoro-3-methyl-1-benzofuran-2-yl)-2-methylpropan-1-oneYield 66%

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 5-fluoro-3-methyl-1-benzofuran (2.0 g) synthesized in Example A67(2) and isobutyryl chloride (1.56 g) in nitromethane (40 mL) was added aluminum chloride (anhydrous) (2.66 g) at 0° C., and the mixture was stirred at 0° C. for 1 hr, and at room temperature for 12 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. After filtration, the filtrate was concentrated. The residue was subjected to silica gel column chromatography (hexane-ethyl acetate 100:0-90:10, v/v) to give the title compound (1.933 g, 66%) as a colorless oil.

Workup

  1. waitat room temperature for 12 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationAfter filtration
  6. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-51515ff4f24240d8bf5b68f24de5550f
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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