Dichloromethane → HCID 66643872, compound

HRID 1186956Notes

Reaction equation

HRID 1186956 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:5]2[C:6](=[O:9])[O:7][CH2:8][C:4]=2[C:3]=1[O:12][CH3:13].[B-](F)(F)(F)[CH:15]=[CH2:16].[K+].ClCCl.C(N(CC)CC)C>C(O)C>[CH3:13][O:12][C:3]1[C:4]2[CH2:8][O:7][C:6](=[O:9])[C:5]=2[CH:10]=[CH:11][C:2]=1[CH:15]=[CH2:16]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 23679353Potassium vinyltrifluoroborateHCID 66643991HCID 66643991, compound

Product 1

HCID 66643872HCID 66643872, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a 100 mL round bottom flask was added 5-Bromo-4-methoxy-2-benzofuran-1(3H)-one (430 mg, 1.8 mmol, 1.0 eq), potassium trifluoro(vinyl)borate (474 g, 3.5 mmol, 2.0 eq), [1,1′-bis(diphenylposphino)-ferrocene]dichloropalladium(II) complex with dichloromethane(1:1) (144 mg, 0.2 mmol, 0.1 eq) and triethylamine (493 μL, 3.5 mmol, 2.0 eq). To above mixture was added ethanol (12 mL). The flask was degassed and filled with nitrogen. The reaction was heated to reflux for 12 hr. The mixture was then diluted with EtOAc, filtered through a pad of celite and washed with brine. The organic phase was dried over Na2SO4, filtered and purified by flash column chromatography using biotage and the solvent systems (0-50% EtOAc/Hexane). The fractions containing desired product were collected and concentrated to 4-methoxy-5-vinyl-2-benzofuran-1(3H)-one.

Workup

  1. customThe flask was degassed
  2. additionfilled with nitrogen
  3. temperatureThe reaction was heated
  4. temperatureto reflux for 12 hr
  5. additionThe mixture was then diluted with EtOAc
  6. filtrationfiltered through a pad of celite
  7. washwashed with brine
  8. dry with materialThe organic phase was dried over Na2SO4
  9. filtrationfiltered
  10. custompurified by flash column chromatography
  11. additionThe fractions containing desired product
  12. customwere collected
  13. concentrationconcentrated to 4-methoxy-5-vinyl-2-benzofuran-1(3H)-one

Sources & evidence

ORD record
ord-59eff91e8cb94734acc56846bacc5dd1
Source dataset
uspto-grants-2014_03
Patent number
US08673920B2

Reaction notes

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