Dichloromethane → HCID 67515714, compound

HRID 2173167Notes

Reaction equation

HRID 2173167 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[O:7][CH2:6][CH2:5]2.[B-](F)(F)(F)[CH:14]=[CH2:15].[K+].ClCCl.C(N(CC)CC)C>C(O)C>[CH:14]([C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[O:7][CH2:6][CH2:5]2)=[CH2:15]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 23679353Potassium vinyltrifluoroborateHCID 441308436-bromo-3,4-dihydro-1H-2-benzopyran-1-one

Product 1

HCID 67515714HCID 67515714, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a 100 mL round bottom flask was added 6-bromo-3,4-dihydro-1H-isochromen-1-one (20 g, 88 mmol, 1.0 eq), potassium trifluoro(vinyl)borate (23.6 g, 176 mmol, 2.0 eq), [1,1′-bis(diphenylposphino)-ferrocene]dichloropalladium(II) complex with dichloromethane(1:1) (7.2 g, 8.8 mmol, 0.1 eq) and triethylamine (24.5 mL, 2.0 eq). To above mixture was added ethanol (400 mL). The flask was degassed and filled with nitrogen. The reaction was heated to reflux under N2 for 10 hr, then cooled and stirred at r.t. for 5 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 give 6-vinyl-3,4-dihydro-1H-isochromen-1-one.

Workup

  1. customThe flask was degassed
  2. additionfilled with nitrogen
  3. temperatureThe reaction was heated
  4. temperatureto reflux under N2 for 10 hr
  5. temperaturecooled
  6. additionThe mixture was then diluted with EtOAc
  7. filtrationfiltered through a pad of Celite®
  8. washwashed with brine
  9. dry with materialThe organic phase was dried over Na2SO4
  10. filtrationfiltered
  11. custompurified by flash column chromatography
  12. additionThe fractions containing desired product
  13. customwere collected
  14. concentrationconcentrated

Sources & evidence

ORD record
ord-45d1f5334aff421aaec5cc07fa2b56e2
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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