2,5-Hexanedione → 1-(2-Fluoro-4-iodophenyl)-2,5-dimethyl-1H-pyrrole

HRID 1884138Notes

Reaction equation

HRID 1884138 reaction equation
[F:1][C:2]1[CH:8]=[C:7]([I:9])[CH:6]=[CH:5][C:3]=1[NH2:4].[CH2:10]([CH2:14][C:15](=O)[CH3:16])[C:11]([CH3:13])=O.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[F:1][C:2]1[CH:8]=[C:7]([I:9])[CH:6]=[CH:5][C:3]=1[N:4]1[C:15]([CH3:16])=[CH:14][CH:10]=[C:11]1[CH3:13]

Participants

6

Reactant 3

HCID 80352,5-HexanedioneHCID 1856942-Fluoro-4-iodoanilineHCID 516892Sodium Bicarbonate

Product 1

HCID 153546301-(2-Fluoro-4-iodophenyl)-2,5-dimethyl-1H-pyrroleYield 98.5%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

A solution of 2-fluoro-4-iodoaniline (25.3 g, 107 mmol), acetonylacetone (14.9 g, 131 mmol) and para-toluenesulfonic acid (203 mg, 1 mmol) in dry toluene was heated under reflux for 1 h with a Dean-Stark tap. After cooling to room temperature the mixture was poured into sodium hydrogen carbonate (saturated). The organic layer was separated, washed with brine, dried over sodium sulfate, filtered and then boiled with charcoal. Filtering to remove the charcoal followed by evaporation afforded the title compound (33.2 g, 98%) as a light brown solid. MS: m/e=315.1 (M++H).

Workup

  1. temperatureunder reflux for 1 h with a Dean-Stark tap
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. filtrationFiltering
  7. customto remove the charcoal
  8. customfollowed by evaporation

Sources & evidence

ORD record
ord-bc2edaa5b07047a8bd17a8a3d32b1917
Source dataset
uspto-grants-2004_07
Patent number
US06762320B2

Reaction notes

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