Bromine → 5-Bromo-3-fluoro-1,2-dihydropyridin-2-one

HRID 1757358Notes

Reaction equation

HRID 1757358 reaction equation
[Br:1]Br.[F:3][C:4]1[C:5]([OH:10])=[N:6][CH:7]=[CH:8][CH:9]=1.[O-]S([O-])=O.[Na+].[Na+]>CN(C)C=O.O>[Br:1][C:8]1[CH:9]=[C:4]([F:3])[C:5]([OH:10])=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 24408BromineHCID 24437Sodium SulfiteHCID 178517712HCID 178517712, compound

Product 1

HCID 1785175945-Bromo-3-fluoro-1,2-dihydropyridin-2-oneYield 90.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

32.0 ml (620.0 mmol) of bromine are added dropwise at 0° C. to 63.7 g (563.2 mmol) of 3-fluoro-2-hydroxypyridine in 700 ml of dimethylformamide. After the mixture has been stirred at room temperature for a further two hours, 800 ml of water are added, and 78 g of Na2SO3 in 350 ml of water are added dropwise. The mixture is then extracted three times with 400 ml of dichloromethane in each case, and the organic phase is dried over Na2SO4 and evaporated to dryness, giving 97.6 g of 5-bromo-3-fluoro-2-hydroxypyridine. ##STR21##

Workup

  1. extractionThe mixture is then extracted three times with 400 ml of dichloromethane in each case
  2. dry with materialthe organic phase is dried over Na2SO4
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-342b5d240a274bc5b49c12f2bb79177c
Source dataset
uspto-grants-1995_08
Patent number
US05445763

Reaction notes

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