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

HRID 2422504ノート

反応式

HRID 2422504 の反応式
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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-894a9d155a3c489e8dbb2b9af34761dc
出典データセット
uspto-grants-2011_06
特許番号
US07960409B2

反応ノート

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