Potassium Carbonate → 1429418-88-1

HRID 1185395Notes

Reaction equation

HRID 1185395 reaction equation
Br[CH2:2][CH2:3][F:4].[N+:5]([C:8]1[CH:9]=[N:10][NH:11][CH:12]=1)([O-:7])=[O:6].C([O-])([O-])=O.[K+].[K+]>CC#N>[F:4][CH2:3][CH2:2][N:10]1[CH:9]=[C:8]([N+:5]([O-:7])=[O:6])[CH:12]=[N:11]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 129822-Fluoroethyl bromideHCID 163764-nitro-1H-pyrazole

Product 1

HCID 584649891429418-88-1Yield 84%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-Bromo-2-fluoroethane (5 g, 38.5 mmol) was added to a stirred mixture of 4-nitro-1H-pyrazole (4.35 g, 38.5 mmol) and K2CO3 (13.3 g, 96.3 mmol) in MeCN (120 mL). The mixture was stirred at room temperature for 30 min and then heated to 50° C. for 18 hr. The mixture was cooled and the solid filtered and washed with MeCN. The filtrate was concentrated under reduced pressure and the crude residue purified via silica gel chromatography (0-100% EtOAc/isohexane) to give 1-(2-fluoroethyl)-4-nitro-1H-pyrazole as a colourless solid (5.13 g, 84%). 1H NMR (400 MHz, CDCl3) δ 8.24 (s, 1H), 8.11 (s, 1H), 4.89-4.72 (m, 2H), 4.57-4.40 (m, 2H)

Workup

  1. temperatureheated to 50° C. for 18 hr
  2. temperatureThe mixture was cooled
  3. filtrationthe solid filtered
  4. washwashed with MeCN
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe crude residue purified via silica gel chromatography (0-100% EtOAc/isohexane)

Sources & evidence

ORD record
ord-49b0d4365f6f4d91888c7a6fe629acef
Source dataset
uspto-grants-2014_03
Patent number
US08669361B2

Reaction notes

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