Ethanol → 8-Bromo-2-phenylquinoline

HRID 1056054ノート

反応式

HRID 1056054 の反応式
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

参加物

9

反応物 4

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

生成物 1

HCID 707004958-Bromo-2-phenylquinoline収率 76%

試薬・触媒・溶媒 4

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-317e579907d64a4197e1aefdb43fc8d2
出典データセット
uspto-grants-2016_07
特許番号
US09394297B2

反応ノート

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