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

HRID 2197069Notes

Reaction equation

HRID 2197069 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-a2114eb5c45746fd9b2232e00ec03ca6
Source dataset
uspto-grants-2012_12
Patent number
US08338462B2

Reaction notes

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