Water → HCID 13579285, compound

HRID 1589094Notes

Reaction equation

HRID 1589094 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]1[CH:4]=[C:5]([CH:9]([C:12]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:13])[C:10]#[N:11])[CH:6]=[CH:7][CH:8]=1.BrBr.[OH2:25]>C(O)(=O)C>[C:15]1([CH:14]2[C:12](=[O:13])[C:9]([C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:21])([F:22])[F:1])[CH:4]=3)=[C:10]([NH2:11])[O:25]2)[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24408BromineHCID 106559Benzenebutanenitrile, .beta.-oxo-.alpha.-[3-(trifluoromethyl)phenyl]-

Product 1

HCID 13579285HCID 13579285, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

In this example a solution containing 21.8 g of (3-trifluoromethylphenyl)-benzylcarbonyl-acetonitrile, dissolved in 60 ml of acetic acid was treated dropwise with a solution of 12.65 g of bromine in 20 ml of glacial acetic acid. The reaction mixture was stirred for about 16 hours at room temperature. The reaction mixture was poured into 250 ml of water and the resulting mixture was extracted three times with ethyl ether. The organic extracts were washed with saturated aqueous sodium bicarbonate, dried over magnesium sulfate and concentrated in vacuo to yield 8.4 g of white solid which was dried affording 7.0 g of the title compound.

Workup

  1. extractionthe resulting mixture was extracted three times with ethyl ether
  2. washThe organic extracts were washed with saturated aqueous sodium bicarbonate
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e8e80ca9ab5f4b218c27e82b6a5df8e0
Source dataset
uspto-grants-1986_02
Patent number
US04568376

Reaction notes

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