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

HRID 489717

Reaction equation

HRID 489717 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)C=O>[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-amine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
122.5 °C

Procedure

A mixture of N,N-dimethyl formamide diisopropyl acetal (1.7 ml, 8.13 mmol) and 1-Bromo-2-fluoro-4-methyl-5-nitro-benzene (1.538 g, 6.57 mmoles) in dry dimethylformamide (10 ml) was heated at 120-125° C. for 1.5 hours. The resulting dark red solution was concentrated under reduced pressure and partitioned between ethyl acetate and water. The organic extract was washed with brine, dried (anhydrous sodium sulfate), and concentrated under reduced pressure to give [2-(4-Bromo-5-fluoro-2-nitro-phenyl)-vinyl]-dimethyl-amine as a dark red solid.

Workup

  1. concentrationThe resulting dark red solution was concentrated under reduced pressure
  2. custompartitioned between ethyl acetate and water
  3. extractionThe organic extract
  4. washwas washed with brine
  5. dry with materialdried (anhydrous sodium sulfate)
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f0aa0231728c40fcbf827b2f84b2a979
Source dataset
uspto-grants-2005_12
Patent number
US06979696B2

Linked notes

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