Dimethylformamide → Methyl 1-(difluoromethyl)pyrrole-2-carboxylate

HRID 876088Notes

Reaction equation

HRID 876088 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([O:8][CH3:9])=[O:7].[F:10][CH:11]([F:13])I.CN(C=O)C.[H-].[Na+]>O>[F:10][CH:11]([F:13])[N:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([O:8][CH3:9])=[O:7]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 136930Methyl pyrrole-2-carboxylateHCID 2775155Difluoro(iodo)methane

Product 1

HCID 86709246Methyl 1-(difluoromethyl)pyrrole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Was prepared from stirred a mixture of methyl 1H-pyrrole-2-carboxylate (3.04 g, 23.5 mmol), difluoroiodomethane (4.4 g, 24.7 mmol) and DMF (40 ml). Sodium hydride (1.41 g, 35.2 mmol) was added in portions during 30 minutes. The mixture was stirred for additional 15 minutes. Water (50 ml) was added and the mixture was extracted with dichloromethane. The mixture was purified by silica gel chromatography, using dichloromethane as solvent. The product was dried and evaporated. Yield 3.21 g (78%).

Workup

  1. customWas prepared
  2. stirringThe mixture was stirred for additional 15 minutes
  3. extractionthe mixture was extracted with dichloromethane
  4. customThe mixture was purified by silica gel chromatography
  5. customThe product was dried
  6. customevaporated

Sources & evidence

ORD record
ord-69186a53844a41978c24028b3943d43c
Source dataset
uspto-grants-2015_03
Patent number
US08986654B2

Reaction notes

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