Water → 2,3-bis(4-fluorophenyl)-1-methyl-1H-pyrrole

HRID 2412949Notes

Reaction equation

HRID 2412949 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[NH:11][CH:12]=[CH:13][C:14]=2[C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)=[CH:6][CH:5]=1.[CH3:22]I.O>CS(C)=O>[F:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]([CH3:22])[CH:12]=[CH:13][C:14]=2[C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 111079192,3-bis(4-fluorophenyl)-1H-pyrrole

Product 1

HCID 128733522,3-bis(4-fluorophenyl)-1-methyl-1H-pyrroleYield 79.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a mixture of 1.5 g (0.038 mole) of 60% sodium hydride dispersion and 100 ml DMSO was added dropwise a solution of 5.1 g (0.02 mole) of 2,3-bis(4-fluorophenyl)-1H-pyrrole in 25 ml DMSO. After the mixture was stirred one hour at room temperature, 5.6 g (0.04 mole) of methyl iodide was added dropwise. The mixture was stirred at room temperature overnight, then poured into water and extracted with ether. The ether extracts were backwashed with water three times, then dried and concentrated. The crude solid was recrystallized from hexane to give 4.3 g of product, m.p. 129°-129.5°.

Workup

  1. stirringThe mixture was stirred at room temperature overnight
  2. extractionextracted with ether
  3. customdried
  4. concentrationconcentrated
  5. customThe crude solid was recrystallized from hexane

Sources & evidence

ORD record
ord-1f7e4052fb0e435685b01c63c08d49c6
Source dataset
uspto-grants-1985_01
Patent number
US04495196

Reaction notes

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