Pyrrole → 3-Fluoro-1-nitro-4-(1H-pyrrol-1-yl)benzene

HRID 56128Notes

Reaction equation

HRID 56128 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[F:11].C([O-])([O-])=O.[K+].[K+].[NH:18]1[CH:22]=[CH:21][CH:20]=[CH:19]1>CS(C)=O.O>[F:11][C:3]1[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=1[N:18]1[CH:22]=[CH:21][CH:20]=[CH:19]1

Participants

6

Reactant 3

HCID 8027PyrroleHCID 11430Potassium CarbonateHCID 1230531,2-Difluoro-4-nitrobenzene

Product 1

HCID 107034583-Fluoro-1-nitro-4-(1H-pyrrol-1-yl)benzeneYield 97%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 1,2-difluoro-4-nitrobenzene (1.59 g, 10 mmol) in DMSO (15 mL) were added K2CO3 (3.04 g, 22 mmol) and pyrrole (0.74 g, 11 mmol) with stirring. The reaction mixture was heated at 90° C. for 18 h, and cooled to rt. The mixture was diluted with water (50 mL), filtered and the filter cake was dried to give the title compound as a yellow solid (2.00 g, 97%).

Workup

  1. temperaturecooled to rt
  2. filtrationfiltered
  3. customthe filter cake was dried

Sources & evidence

ORD record
ord-d97e250c56b54b6ea7fde21ea169c008
Source dataset
uspto-grants-2016_09
Patent number
US09434695B2

Reaction notes

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