반응식
Br[C:2]1[CH:3]=[C:4]([O:8][C:9]([F:12])([F:11])[F:10])[CH:5]=[CH:6][CH:7]=1.C([Li])(C)(C)C.Br[C:19]1[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][N:20]=1.[OH-].[NH4+]>C1COCC1.CCCCC.C(OCC)C.[Cl-].[Zn+2].[Cl-].[Ni].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[F:10][C:9]([F:12])([F:11])[O:8][C:4]1[CH:3]=[C:2]([C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][N:20]=2)[CH:7]=[CH:6][CH:5]=1참가 물질
반응물 4
생성물 1
시약·촉매·용매 5
반응 조건
- 온도
- -78 °C
실험 절차
To a solution of 3-bromotrifluoromethoxybenzene (0.590 mL, 4.00 mmol) in THF (12 mL) at -78° C. was added t-butyl lithium (4.71 mL, of a 1.7M solution in pentane, 8.00 mmol. After 10 minutes zinc chloride(4.0 mL, of a 1M solution in diethylether, 4.00 mmol) was added. The reaction was stirred for 10 minutes at -78° C. and then allowed to warm to 0° C. and stirred for 30 minutes. This solution was added via cannula to a solution of 2-bromo-5-methyl pyridine and bis(triphenylphosphine) Nickel II chloride. The reaction stirred for 1 hour at 0° C. and then at ambient temperature for a furthur 1 hour. Saturated ammonium hydroxide solution (3 mL) was added and the mixture stirred until homogenous, extracted with Et2O and the organic extracts washed with saturated brine, dried (MgSO4) and evaporated in vacuo. The residue was chromatographed (Silica gel, 25-50% CH2Cl2 in hexanes).
후처리
- temperatureto warm to 0° C.
- stirringstirred for 30 minutes
- stirringThe reaction stirred for 1 hour at 0° C.
- waitat ambient temperature for a furthur 1 hour
- stirringthe mixture stirred until homogenous,
- extractionextracted with Et2O
- washthe organic extracts washed with saturated brine
- dry with materialdried (MgSO4)
- customevaporated in vacuo
- customThe residue was chromatographed (Silica gel, 25-50% CH2Cl2 in hexanes)
출처 및 근거
- ORD 기록
- ord-89439644dad44269915f26bafa0e3617
- 출처 데이터셋
- uspto-grants-1999_02
- 특허 번호
- US05872136
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