Ethanol → 5-Chloro-2-ethenylpyridine

HRID 15052

Reaction equation

HRID 15052 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][N:3]=1.[CH:9]([B-](F)(F)F)=[CH2:10].[K+].C(N(CC)CC)C.C(O)C>[Pd+2].ClC1C=C[C-](P(C2C=CC=CC=2)C2C=CC=CC=2)C=1Cl.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].C(OCC)(=O)C>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]([CH:9]=[CH2:10])=[N:3][CH:4]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 8471TriethylamineHCID 276852,5-DichloropyridineHCID 23679353Potassium vinyltrifluoroborate

Product 1

HCID 155476265-Chloro-2-ethenylpyridineYield 69%

Reagents, catalysts & solvents 2

HCID 178478230HCID 178478230, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2,5-dichloropyridine (10.0 g), potassium vinyltrifluoroborate (10.86 g), dichloromethane complex (2.5 g) of dichloro-1,1′-bis(diphenylphosphino)-ferrocene palladium (II), triethylamine (14.13 mL) and ethanol (150 mL) was stirred overnight under reflux. After cooling the system to room temperature, ethyl acetate was added, followed by washing with saturated aqueous sodium hydrogencarbonate solution and saturated brine and drying over anhydrous sodium sulfate. Concentrating the solvent under reduced pressure, the resulting residue was distilled under reduced pressure (63° C., 8 mmHg) to provide the title compound (6.50 g, 69%).

Workup

  1. temperatureunder reflux
  2. washby washing with saturated aqueous sodium hydrogencarbonate solution and saturated brine
  3. dry with materialdrying over anhydrous sodium sulfate
  4. concentrationConcentrating the solvent under reduced pressure
  5. distillationthe resulting residue was distilled under reduced pressure (63° C., 8 mmHg)

Sources & evidence

ORD record
ord-9ed94748395b45b697f76c4f2d4a5178
Source dataset
uspto-grants-2010_06
Patent number
US07732456B2

Linked notes

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