Water → N-[2-bromo-4-[3-(3,5-dichlorophenyl)-4,4,4-trifluoro-3-(nitromethyl) butanoyl]phenylmethyl]phthalimide

HRID 2386157Notes

Reaction equation

HRID 2386157 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([C:8](=[O:23])[CH:9]=[C:10]([C:15]2[CH:20]=[C:19]([Cl:21])[CH:18]=[C:17]([Cl:22])[CH:16]=2)[C:11]([F:14])([F:13])[F:12])[CH:5]=[CH:4][C:3]=1[CH2:24][N:25]1[C:29](=[O:30])[C:28]2=[CH:31][CH:32]=[CH:33][CH:34]=[C:27]2[C:26]1=[O:35].[N+:36]([CH3:39])([O-:38])=[O:37].C1CCN2C(=NCCC2)CC1.O>C(#N)C>[Br:1][C:2]1[CH:7]=[C:6]([C:8](=[O:23])[CH2:9][C:10]([C:15]2[CH:20]=[C:19]([Cl:21])[CH:18]=[C:17]([Cl:22])[CH:16]=2)([CH2:39][N+:36]([O-:38])=[O:37])[C:11]([F:14])([F:13])[F:12])[CH:5]=[CH:4][C:3]=1[CH2:24][N:25]1[C:26](=[O:35])[C:27]2=[CH:34][CH:33]=[CH:32][CH:31]=[C:28]2[C:29]1=[O:30]

Participants

6

Reactant 4

HCID 962WaterHCID 6375NitromethaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 86648069N-[2-bromo-4-[3-(3,5-dichlorophenyl)-4,4,4-trifluoro-2-butenoyl]phenylmethyl]phthalimide

Product 1

HCID 86648070N-[2-bromo-4-[3-(3,5-dichlorophenyl)-4,4,4-trifluoro-3-(nitromethyl) butanoyl]phenylmethyl]phthalimide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 0.80 g of N-[2-bromo-4-[3-(3,5-dichlorophenyl)-4,4,4-trifluoro-2-butenoyl]phenylmethyl]phthalimide and 0.12 g of nitromethane in 10 mL of acetonitrile, 0.23 g of 1,8-diazabicyclo[5,4,0]-7-undecene was added and the resultant reaction mixture was stirred at room temperature for 15 hours. After the completion of the reaction, 20 mL of water was added to the reaction mixture and the resultant reaction mixture was extracted with ethyl acetate (30 mL×2). The organic phase was dehydrated and dried over a saturated brine and anhydrous magnesium sulfate in this order and the solvent was distilled off under reduced pressure to obtain 0.90 g of the objective substance as a yellow resinoid.

Workup

  1. customthe resultant reaction mixture
  2. additionwas added to the reaction mixture
  3. customthe resultant reaction mixture
  4. extractionwas extracted with ethyl acetate (30 mL×2)
  5. dry with materialdried over a saturated brine and anhydrous magnesium sulfate in this order
  6. distillationthe solvent was distilled off under reduced pressure
  7. customto obtain 0.90 g of the objective substance as a yellow resinoid

Sources & evidence

ORD record
ord-0f872f93af16433980b6548412036ddd
Source dataset
uspto-grants-2012_09
Patent number
US08268754B2

Reaction notes

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