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

HRID 873324Notes

Reaction equation

HRID 873324 reaction equation
[F:1][C:2]1[C:3]([OH:8])=[N:4][CH:5]=[CH:6][CH:7]=1.[Br:9]Br>CN(C=O)C>[Br:9][C:6]1[CH:7]=[C:2]([F:1])[C:3]([OH:8])=[N:4][CH:5]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 178517712HCID 178517712, compound

Product 1

HCID 1785175945-Bromo-3-fluoro-1,2-dihydropyridin-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of 3-fluoro-2-hydroxypyridine (1 g, 8.8 mmol) in dry DMF (11 mL) was cooled in an ice bath. Bromine (1.55 g, 9.7 mmol) was added drop-wise over a period of 10 min and the reaction mixture stirred at 0° C. for 1 h then allowed to warm to room temperature and stirred for an additional 2 h. The reaction was quenched with water. The aqueous was extracted with DCM (×4) and the combined organics dried (MgSO4) and concentrated in vacuo. Purification by column chromatography (gradient: 20-100% EtOAc in pet. ether 40-60) yielded 5-Bromo-3-fluoro-2-hydroxypyridine as a pale yellow solid.

Workup

  1. temperaturewas cooled in an ice bath
  2. temperatureto warm to room temperature
  3. stirringstirred for an additional 2 h
  4. customThe reaction was quenched with water
  5. extractionThe aqueous was extracted with DCM (×4)
  6. dry with materialthe combined organics dried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customPurification by column chromatography (gradient: 20-100% EtOAc in pet. ether 40-60)

Sources & evidence

ORD record
ord-b8698e78415242adbe212df2cab06a42
Source dataset
uspto-grants-2015_03
Patent number
US08975406B2

Reaction notes

Loading…