Pyrrolidine → 1-[2-(2-Bromo-4-fluoro-6-nitro-phenyl)-vinyl]-pyrrolidine

HRID 2365201Notes

Reaction equation

HRID 2365201 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([N+:9]([O-:11])=[O:10])[C:3]=1[CH3:12].CO[CH:15](OC)[N:16]([CH3:18])[CH3:17].N1CC[CH2:23][CH2:22]1>CN(C)C=O.C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([N+:9]([O-:11])=[O:10])[C:3]=1[CH:12]=[CH:18][N:16]1[CH2:15][CH2:23][CH2:22][CH2:17]1

Participants

6

Reactant 3

HCID 31268PyrrolidineHCID 78373Dimethylformamide dimethyl acetalHCID 27733851-Bromo-5-fluoro-2-methyl-3-nitrobenzene

Product 1

HCID 866380951-[2-(2-Bromo-4-fluoro-6-nitro-phenyl)-vinyl]-pyrrolidine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 1-bromo-5-fluoro-2-methyl-3-nitro-benzene (1.78 g) in dimethylformamide (15 ml) was added dimethylformamide dimethyl acetal (3.0 ml) followed by pyrrolidine (0.63 ml) and heated to 110° C. After 24 hours the cooled reaction mixture was diluted with ethyl acetate, washed with water, brine, dried (MgSO4) and the solvent removed in vacuo to yield crude 1-[2-(2-bromo-4-fluoro-6-nitro-phenyl)-vinyl]-pyrrolidine.

Workup

  1. customAfter 24 hours the cooled reaction mixture
  2. washwashed with water, brine
  3. dry with materialdried (MgSO4)
  4. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-32059d4aaf474813ac132748fe96ad33
Source dataset
uspto-grants-2014_04
Patent number
US08697693B2

Reaction notes

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