Tricyclohexylphosphine → 7-bromo-4-(3-methylphenyl)-2H-chromen-2-one

HRID 2422504Notes

Reaction equation

HRID 2422504 reaction equation
FC(F)(F)S(O[C:7]1[C:16]2[C:11](=[CH:12][C:13]([Br:17])=[CH:14][CH:15]=2)[O:10][C:9](=[O:18])[CH:8]=1)(=O)=O.[CH3:21][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>[Br:17][C:13]1[CH:12]=[C:11]2[C:16]([C:7]([C:26]3[CH:25]=[CH:24][CH:23]=[C:22]([CH3:21])[CH:27]=3)=[CH:8][C:9](=[O:18])[O:10]2)=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 75806TricyclohexylphosphineHCID 522689Potassium FluorideHCID 27339503-Tolylboronic acidHCID 194269487-bromo-2-oxo-2H-chromen-4-yl trifluoromethanesulfonate

Product 1

HCID 866219677-bromo-4-(3-methylphenyl)-2H-chromen-2-one

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 7-bromo-2-oxo-2H-chromen-4-yl trifluoromethanesulfonate (prepared as described in U.S. Pat. No. 5,552,437) (1.1 g, 3.0 mmol) and 3-methylbenzeneboronic acid (450 mg, 3.3 mmol) in THF (12 mL), tricyclohexylphosphine (30 mg, 0.1 mmol) and potassium fluoride (574 mg, 9.9 mmol) were added. The reaction mixture was purged twice with nitrogen before palladium (II) acetate (20 mg, 0.1 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): 7.67 (s, 1H), 7.53-7.33 (m, 6H), 6.40 (s, 1H), 2.46 (s, 3H).

Workup

  1. additionwas added
  2. filtrationwas 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-894a9d155a3c489e8dbb2b9af34761dc
Source dataset
uspto-grants-2011_06
Patent number
US07960409B2

Reaction notes

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