Water → HCID 59186922, compound

HRID 2090187Notes

Reaction equation

HRID 2090187 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([O:10][C:11]([F:14])([F:13])[F:12])[CH:3]=1.O.[CH3:16][N:17](C=O)C>[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:6]([C:5]1[CH:8]=[CH:9][C:2]([C:16]#[N:17])=[CH:3][C:4]=1[O:10][C:11]([F:14])([F:13])[F:12])=[O:7]

Participants

6

Reactant 3

HCID 962WaterHCID 6228DimethylformamideHCID 187000874-Bromo-2-(trifluoromethoxy)benzaldehyde

Product 1

HCID 59186922HCID 59186922, compound

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalyst

Procedure

10.63 g (39.51 mmol) of 4-bromo-2-(trifluoromethoxy)benzaldehyde, 3.43 g (29.24 mmol) of zinc cyanide and 1.37 g (1.19 mmol) of tetrakis(triphenylphosphine)palladium(0) are dissolved in 80 ml of DMF. The reaction mixture is then reacted in several portions in a single mode microwave (Emrys Optimizer, 5 min at 220° C.). The combined mixtures are mixed with water and extracted twice with toluene. The combined organic phases are washed with saturated sodium chloride solution and dried with sodium sulfate, and then the solvent is removed in a rotary evaporator. The residue is purified by column chromatography (silica gel, mobile phase: cyclohexane/ethyl acetate 10:1). 3.32 g (78% of theory) of the title compound are obtained with a purity of 80% (according to LC-MS).

Workup

  1. customThe reaction mixture is then reacted in several portions in a single mode microwave (Emrys Optimizer, 5 min at 220° C.)
  2. extractionextracted twice with toluene
  3. washThe combined organic phases are washed with saturated sodium chloride solution
  4. dry with materialdried with sodium sulfate
  5. customthe solvent is removed in a rotary evaporator
  6. customThe residue is purified by column chromatography (silica gel, mobile phase: cyclohexane/ethyl acetate 10:1)

Sources & evidence

ORD record
ord-dae9aa54133646d29d8dd50b430818b4
Source dataset
uspto-grants-2013_05
Patent number
US08436180B2

Reaction notes

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