N,N,N-trimethyl-1,1-bis(1-methylethoxy)amine → [2-(4-Bromo-5-fluoro-2-nitro-phenyl)-vinyl]-dimethyl-amine

HRID 222470

Reaction equation

HRID 222470 reaction equation
C(O[CH:5](OC(C)C)[N:6]([CH3:8])[CH3:7])(C)C.[Br:13][C:14]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[C:17]([CH3:23])=[CH:16][C:15]=1[F:24]>CN(C=O)C>[Br:13][C:14]1[C:15]([F:24])=[CH:16][C:17]([CH:23]=[CH:5][N:6]([CH3:7])[CH3:8])=[C:18]([N+:20]([O-:22])=[O:21])[CH:19]=1

Participants

4

Reactant 2

HCID 87682N,N,N-trimethyl-1,1-bis(1-methylethoxy)amineHCID 27793654-Bromo-5-fluoro-2-nitrotoluene

Product 1

HCID 73878710[2-(4-Bromo-5-fluoro-2-nitro-phenyl)-vinyl]-dimethyl-amineYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
125 °C

Procedure

A mixture of N,N-dimethylformamide diisopropyl acetal (1.32 mL, 6.31 mmol) and 1-bromo-2-fluoro-4-methyl-5-nitro-benzene (1.23 g, 5.26 mmol) in dry DMF (15.0 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-bromo-5-fluoro-2-nitro-phenyl)-vinyl]-dimethyl-amine as dark red solid (1.89 mg, 83%). 1H NMR (CDCl3, 400 MHz): 2.92 (s, 6H), 5.88 (d, J=12.3 Hz, 1H), 6.98 (d, J=13.2 Hz, 1H), 7.11 (d, J=10.8 Hz, 1H), 8.10 (d, J=6.9 Hz, 1H).

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-1b9b703a6db84966ac7373889bb196cb
Source dataset
uspto-grants-2012_06
Patent number
US08207216B2

Linked notes

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