Water → HCID 22118007, compound

HRID 1620524Notes

Reaction equation

HRID 1620524 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([C:10]([F:13])([F:12])[F:11])[CH:3]=1.[Cu][C:15]#[N:16].O.C(OCC)C>CN1CCCC1=O>[CH:6]([C:5]1[CH:8]=[CH:9][C:2]([C:15]#[N:16])=[CH:3][C:4]=1[C:10]([F:13])([F:12])[F:11])=[O:7]

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 121872184-Bromo-2-(trifluoromethyl)benzaldehydeHCID 178418546HCID 178418546, compound

Product 1

HCID 22118007HCID 22118007, compoundYield 38.8%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
200 °C

Procedure

To a solution of 4-bromo-2-(trifluoromethyl)benzaldehyde (2.0 g) in N-methylpyrrolidin-2-one (39.5 mL) was added copper(I) cyanide (1.42 g). The reaction mixture was stirred at 200° C. for 3 hr, allowed to cool to room temperature, poured into water, and diethyl ether was added. The insoluble material was removed by filtration through celite. The organic layer of the filtrate was separated, washed with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (0.610 g).

Workup

  1. temperatureto cool to room temperature
  2. additionwas added
  3. customThe insoluble material was removed by filtration through celite
  4. customThe organic layer of the filtrate was separated
  5. washwashed with water and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-5b4a2fc46b654453a85b598943d45e3d
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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