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

HRID 2070363Notes

Reaction equation

HRID 2070363 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-acee84b6d4c2481da3aac29a53a69e01
Source dataset
uspto-grants-2012_10
Patent number
US08299261B2

Reaction notes

Loading…