Tricyclohexylphosphine → 4-(3-fluorophenyl)-7-methyl-2H-chromen-2-one

HRID 2422482Notes

Reaction equation

HRID 2422482 reaction equation
FC(F)(F)S(O[C:7]1[C:16]2[C:11](=[CH:12][C:13]([CH3:17])=[CH:14][CH:15]=2)[O:10][C:9](=[O:18])[CH:8]=1)(=O)=O.[F:21][C:22]1[CH:23]=[C:24](B(O)O)[CH:25]=[CH:26][CH:27]=1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.[F-].[K+]>C1COCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:21][C:22]1[CH:27]=[C:26]([C:7]2[C:16]3[C:11](=[CH:12][C:13]([CH3:17])=[CH:14][CH:15]=3)[O:10][C:9](=[O:18])[CH:8]=2)[CH:25]=[CH:24][CH:23]=1

Participants

7

Reactant 4

HCID 75806TricyclohexylphosphineHCID 522689Potassium FluorideHCID 27339863-Fluorophenylboronic acidHCID 233702387-Methyl-2-oxo-2H-chromen-4-YL trifluoromethanesulfonate

Product 1

HCID 569716744-(3-fluorophenyl)-7-methyl-2H-chromen-2-one

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 7-methyl-2-oxo-2H-chromen-4-yl trifluoromethanesulfonate (5 g, 16.2 mmol) and 3-fluorobenzeneboronic acid (2.5 g, 17.9 mmol) in THF (75 mL), tricyclohexylphosphine (227 mg, 0.81 mmol) and potassium fluoride (3.3 g, 56.8 mmol) were added. The reaction mixture was purged twice with nitrogen before palladium (II) acetate (146 mg, 0.65 mmol) was added. After 16 hours stirring at room temperature, the reaction mixture was filtered over celite and the filtrate was concentrated under reduced pressure. The crude residue obtained was purified by column chromatography (CH2Cl2/Hexanes, 70:30). To afford the title compound 1H NMR (400 MHz, acetone-d6): 7.7-7.6 (m, 1H), 7.45-7.3 (m, 4H), 7.26 (s, 1H), 7.18 (d, 1H), 6.3 (s, 1H), 2.47 (s, 3H).

Workup

  1. additionwas added
  2. filtrationthe reaction mixture was filtered over celite
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe crude residue obtained
  5. customwas purified by column chromatography (CH2Cl2/Hexanes, 70:30)

Sources & evidence

ORD record
ord-4873e2ca703f4ed7bb86616feddff5c5
Source dataset
uspto-grants-2011_06
Patent number
US07960409B2

Reaction notes

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