Ethanol → 8-Bromo-2-phenylquinoline

HRID 1056054

반응식

HRID 1056054 반응식
Br[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([Br:12])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.CCO.C([O-])([O-])=O.[Na+].[Na+].[C:22]1(B(O)O)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C1(C)C=CC=CC=1.CCOC(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[Br:12][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:4]=1[N:3]=[C:2]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH:11]=[CH:10]2

참가 물질

9

반응물 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 459259512,8-Dibromoquinoline

생성물 1

HCID 707004958-Bromo-2-phenylquinoline수율 76%

시약·촉매·용매 4

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

실험 절차

To a mixture of 2,8-dibromoquinoline (1.0 g, 3.49 mmol), Pd(PPh3)4 (0.2 g, 0.174 mmol) in toluene:EtOH:H2O (10 mL:1 mL:1 mL) under argon atmosphere was added Na2CO3 (0.44 g, 4.18 mmol) and phenyl boronic acid (0.507 g, 4.18 mmol) and the reaction was heated to reflux for 24 h. The mixture was cooled to RT and diluted with EtOAc (50 mL), washed with water and brine (50 mL). The organic layer was dried, filtered and concentrated. The residue was purified by column chromatography (10:1 hexane:EtOAc) to give 8-bromo-2-phenylquinoline (0.75 g, 76%) as pale brown oil. MS (ESI, pos. ion) m/z: 284.0 (M+1).

후처리

  1. temperaturethe reaction was heated
  2. temperatureto reflux for 24 h
  3. washwashed with water and brine (50 mL)
  4. customThe organic layer was dried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography (10:1 hexane:EtOAc)

출처 및 근거

ORD 기록
ord-317e579907d64a4197e1aefdb43fc8d2
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09394297B2

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