Water → 1-(Benzofuran-6-yl)ethanone

HRID 1038581

Reaction equation

HRID 1038581 reaction equation
Br[C:2]1[CH:10]=[CH:9][C:5]2[CH:6]=[CH:7][O:8][C:4]=2[CH:3]=1.BrC1C2[O:19][CH:18]=[CH:17]C=2C=CC=1.C([Sn](CCCC)(CCCC)C(OCC)=C)CCC.O>C1(C)C=CC=CC=1>[O:8]1[C:4]2[CH:3]=[C:2]([C:18](=[O:19])[CH3:17])[CH:10]=[CH:9][C:5]=2[CH:6]=[CH:7]1

Participants

6

Reactant 4

HCID 962WaterHCID 1136287-Bromo-1-benzofuranHCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 151587226-Bromo-1-benzofuran

Product 1

HCID 451226521-(Benzofuran-6-yl)ethanone

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of a mixture of 6-bromobenzofuran and 7-bromobenzofuran (1.12 g, 5.68 mmol) in toluene (19 mL), tetrakistriphenyl phosphine palladium (650 mg, 0.57 mmol) and tributyl(1-ethoxyvinyl)tin (2.11 mL, 6.25 mmol) were added, and the mixture was stirred at 100° C. overnight. The reaction solution was added water at room temperature, and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, concentrated in vacuo, and purified by silica-gel column chromatography (hexane). The title compound (280 mg) was obtained as a yellow crystal.

Workup

  1. additionwere added
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. custompurified by silica-gel column chromatography (hexane)

Sources & evidence

ORD record
ord-7d62b5426707465aa5dcf79924b3498a
Source dataset
uspto-grants-2013_10
Patent number
US08551985B2

Linked notes

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