Water → Ethyl 2-bromo-5-fluoroisonicotinate

HRID 1516575Notes

Reaction equation

HRID 1516575 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]([F:11])=[CH:9][N:10]=1)[C:5]([OH:7])=[O:6].C(=O)([O-])[O-].[K+].[K+].I[CH2:19][CH3:20].O>CN(C)C=O>[CH2:19]([O:6][C:5](=[O:7])[C:4]1[C:8]([F:11])=[CH:9][N:10]=[C:2]([Br:1])[CH:3]=1)[CH3:20]

Participants

6

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 467392772-Bromo-5-fluoroisonicotinic acid

Product 1

HCID 46311464Ethyl 2-bromo-5-fluoroisonicotinateYield 49.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-bromo-5-fluoroisonicotinic acid (5.2 g) in N,N-dimethylformamide (100 mL) were added potassium carbonate (9.8 g) and iodoethane (7.4 g) at room temperature, and this mixture was stirred at same temperature for 24 hours. This reaction mixture was poured into water, and this mixture was extracted with ethyl acetate. This organic layer was washed with water and brine, dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to give the title compound (2.9 g).

Workup

  1. extractionthis mixture was extracted with ethyl acetate
  2. washThis organic layer was washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-6698df2d4dba451db6f831b02125bd08
Source dataset
uspto-grants-2012_07
Patent number
US08227500B2

Reaction notes

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