2,3-DIFLUORO-4-IODOPYRIDINE → 3-Fluoro-4-iodopyridin-2(1H)-one

HRID 1475876Notes

Reaction equation

HRID 1475876 reaction equation
F[C:2]1[C:7]([F:8])=[C:6]([I:9])[CH:5]=[CH:4][N:3]=1.C(O)(=[O:12])C.O>>[F:8][C:7]1[C:2](=[O:12])[NH:3][CH:4]=[CH:5][C:6]=1[I:9]

Participants

3

Reactant 2

HCID 114478372,3-DIFLUORO-4-IODOPYRIDINEHCID 21899381Acetic acid--water (1/1)

Product 1

HCID 708173253-Fluoro-4-iodopyridin-2(1H)-oneYield 71.4%

Procedure

2,3-Difluoro-4-iodopyridine (300 mg, 1.24 mmol) was suspended in acetic acid:water (2:1, 15 mL). The mixture was heated to reflux and stirred at this temperature overnight. Reaction was concentrated to dryness, and triturated in water (10 mL) for 30 min. The solid was collected via filtration, washed with water (2×10 mL), and pentane (2×20 mL) and dried under vacuum to afford the title compound as a white solid (354 mg, 71.4%). LC-MS m/z 342.0 (M+1). 1H NMR (400 MHz, METHANOL-d4) δ ppm 6.56-6.82 (m, 1H) 6.83-7.18 (m, 1H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. customReaction
  4. concentrationwas concentrated to dryness
  5. customtriturated in water (10 mL) for 30 min
  6. filtrationThe solid was collected via filtration
  7. washwashed with water (2×10 mL), and pentane (2×20 mL)
  8. customdried under vacuum

Sources & evidence

ORD record
ord-19d856e44ea4447d9abb93bdf471c6b3
Source dataset
uspto-grants-2015_04
Patent number
US09018384B2

Reaction notes

Loading…