Dimethylformamide dimethyl acetal → [2-(4-Iodo-5-fluoro-2-nitro-phenyl)-vinyl]-dimethyl-amine

HRID 222467Notes

Reaction equation

HRID 222467 reaction equation
CO[CH:3](OC)[N:4]([CH3:6])[CH3:5].[I:9][C:10]1[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[C:13]([CH3:19])=[CH:12][C:11]=1[F:20]>CN(C=O)C>[I:9][C:10]1[C:11]([F:20])=[CH:12][C:13]([CH:19]=[CH:3][N:4]([CH3:6])[CH3:5])=[C:14]([N+:16]([O-:18])=[O:17])[CH:15]=1

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 226127641-Fluoro-2-iodo-5-methyl-4-nitrobenzene

Product 1

HCID 72526988[2-(4-Iodo-5-fluoro-2-nitro-phenyl)-vinyl]-dimethyl-amineYield 62%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
125 °C

Procedure

A mixture of N,N-dimethylformamide dimethyl acetal (0.30 mL, 2.31 mmol) and 1-iodo-2-fluoro-4-methyl-5-nitro-benzene (0.50 g, 1.78 mmol) in dry DMF (3.0 mL) was stirred at 125° C. for 3 h. The resulting mixture was partitioned between EtOAc and water. The organic layer was washed with brine, dried over MgSO4, filtered, and concentrated. The residue was washed with hexane to give [2-(4-iodo-5-fluoro-2-nitro-phenyl)-vinyl]-dimethyl-amine as dark red solid (0.37 mg, 62%). 1H NMR (CDCl3, 400 MHz): 2.97 (s, 6H), 5.92 (d, J=13.3 Hz, 1H), 7.02 (d, J=13.3 Hz, 1H), 7.09 (d, J=10.2 Hz, 1H), 8.30 (d, J=6.2 Hz, 1H). 13C NMR (CDCl3, 100 MHz,): 40.8, 108.9, 109.1, 137.0, 139.3, 146.0.

Workup

  1. customThe resulting mixture was partitioned between EtOAc and water
  2. washThe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. washThe residue was washed with hexane

Sources & evidence

ORD record
ord-3fdb0c8bb28d490697a4c79e988bf556
Source dataset
uspto-grants-2012_06
Patent number
US08207216B2

Reaction notes

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