Hydrogen chloride-ethyl acetate → ethyl 2-chloro-5-(2,6-difluorophenyl)-1H-pyrrole-3-carboxylate

HRID 2090674Notes

Reaction equation

HRID 2090674 reaction equation
[C:1]([CH:3]([CH2:9][C:10]([C:12]1[C:17]([F:18])=[CH:16][CH:15]=[CH:14][C:13]=1[F:19])=O)[C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2].C(OCC)(=O)C.[ClH:26]>C(OCC)(=O)C>[Cl:26][C:1]1[NH:2][C:10]([C:12]2[C:17]([F:18])=[CH:16][CH:15]=[CH:14][C:13]=2[F:19])=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 66974573Ethyl 2-cyano-4-(2,6-difluorophenyl)-4-oxobutanoate

Product 1

HCID 66974607ethyl 2-chloro-5-(2,6-difluorophenyl)-1H-pyrrole-3-carboxylateYield 68%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution (14 mL) of ethyl 2-cyano-4-(2,6-difluorophenyl)-4-oxobutanoate (13.83 g) in ethyl acetate was added dropwise to 4 mol/L hydrogen chloride-ethyl acetate solution (100 mL) at 10-15° C. The mixture was stirred at room temperature for 12 hr, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=9:1→8:2) to give the title compound as yellow crystals (yield 10.0 g, 68%).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=9:1→8:2)

Sources & evidence

ORD record
ord-c254a1b5060a41899082492b16b75ad6
Source dataset
uspto-grants-2013_05
Patent number
US08436187B2

Reaction notes

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