Water → 1-[3-(benzyloxy)-4-nitrophenyl]-3,4-difluoro-1H-pyrrole

HRID 1528056Notes

Reaction equation

HRID 1528056 reaction equation
[F:1][C:2]1[C:6]([F:7])=[CH:5][N:4]([C:8]2[CH:9]=[CH:10][C:11]([N+:15]([O-:17])=[O:16])=[C:12]([OH:14])[CH:13]=2)[CH:3]=1.[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[CH2:18]([O:14][C:12]1[CH:13]=[C:8]([N:4]2[CH:3]=[C:2]([F:1])[C:6]([F:7])=[CH:5]2)[CH:9]=[CH:10][C:11]=1[N+:15]([O-:17])=[O:16])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 712721575-(3,4-difluoro-1H-pyrrol-1-yl)-2-nitrophenol

Product 1

HCID 712722201-[3-(benzyloxy)-4-nitrophenyl]-3,4-difluoro-1H-pyrrole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 5-(3,4-difluoro-1H-pyrrol-1-yl)-2-nitrophenol (6.39 g), benzyl bromide (3.48 mL) and potassium carbonate (5.51 g) in DMF (60 mL) was stirred at room temperature overnight. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was recrystallized from hexane/ethyl acetate to give the title compound (8.57 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was recrystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-8a7264e7d65c4353bb8ac31803901f1e
Source dataset
uspto-grants-2015_07
Patent number
US09090586B2

Reaction notes

Loading…