2-Fluoropyridine → HCID 68582493, compound

HRID 645593Notes

Reaction equation

HRID 645593 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1[OH:10].C([O-])([O-])=O.[K+].[K+].F[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1>CN(C)C=O.C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1[O:10][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1

Participants

6

Reactant 3

HCID 97462-Fluoropyridine2×HCID 11430Potassium CarbonateHCID 27362882-Bromo-4,5-difluorophenol

Product 1

HCID 68582493HCID 68582493, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 2-bromo-4,5-difluoro-phenol (1 g, 4.78 mmol) in N,N-dimethylformamide were added K2CO3 and 2-fluoropyridine (0.46 g, 4.78 mmol) and heated at 120° C. for overnight. One more equivalent of 2-fluoropyridine was added and heated at 150° C. for 12 h. The reaction mixture was dissolved in ethyl acetate, washed with 1M NaHCO3, concentrated and purified by flash column chromatography using 0%, 5% and 10% of ethyl acetate in hexanes to yield 0.8 g (59%) of product. MS (ESI+) m/z 286 (M+H)+.

Workup

  1. temperatureheated at 150° C. for 12 h
  2. washwashed with 1M NaHCO3
  3. concentrationconcentrated
  4. custompurified by flash column chromatography

Sources & evidence

ORD record
ord-9057631dd2824f658e3cab2c0de0c24f
Source dataset
uspto-grants-2010_04
Patent number
US07704997B1

Reaction notes

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