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

HRID 2422504노트

반응식

HRID 2422504 반응식
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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-894a9d155a3c489e8dbb2b9af34761dc
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07960409B2

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