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

HRID 1782205Notes

Reaction equation

HRID 1782205 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-7497cdae865947da87330c33767b9096
Source dataset
uspto-grants-2009_03
Patent number
US07498337B2

Reaction notes

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