Ethanol → 8-Bromo-2-phenylquinoline

HRID 1056054Notes

Reaction equation

HRID 1056054 reaction equation
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

Participants

9

Reactant 4

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

Product 1

HCID 707004958-Bromo-2-phenylquinolineYield 76%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-317e579907d64a4197e1aefdb43fc8d2
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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