Hydrogen chloride-ethyl acetate → Ethyl 2-chloro-5-(2-fluorophenyl)-1H-pyrrole-3-carboxylate

HRID 554209Notes

Reaction equation

HRID 554209 reaction equation
[C:1]([CH:3]([CH2:9][C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[F:18])=O)[C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2].C(OCC)(=O)C.[ClH:25]>>[Cl:25][C:1]1[NH:2][C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[F:18])=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

3

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 66924657Ethyl 2-cyano-4-(2-fluorophenyl)-4-oxobutanoate

Product 1

HCID 66924835Ethyl 2-chloro-5-(2-fluorophenyl)-1H-pyrrole-3-carboxylateYield 53%

Procedure

A mixture of ethyl 2-cyano-4-(2-fluorophenyl)-4-oxobutanoate (19.3 g) and 4 mol/L hydrogen chloride-ethyl acetate solution (100 mL) was stirred at room temperature for 18 hr. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=10:1→3:1) to give the title compound as a brown solid (yield 8.76 g, 53%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=10:1→3:1)

Sources & evidence

ORD record
ord-e0d6c2a5292647a0aab95f58bacd676c
Source dataset
uspto-grants-2011_11
Patent number
US08048909B2

Reaction notes

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