Water → HCID 86678825, compound

HRID 1620660Notes

Reaction equation

HRID 1620660 reaction equation
[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[C:7]([C:12]([F:15])([F:14])[F:13])[CH:6]=1)(=[O:3])[CH3:2].[Br:16]N1C(=O)CCC1=O.O>FC(C1C=CC=CC=1)(F)F.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][Br:16])=[C:7]([C:12]([F:13])([F:14])[F:15])[CH:6]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 86678824HCID 86678824, compound

Product 1

HCID 86678825HCID 86678825, compoundYield 68.1%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 7368(Trifluoromethyl)benzeneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 4-methyl-3-(trifluoromethyl)phenyl acetate (6.04 g) and 75% benzoyl peroxide (0.45 g) in (trifluoromethyl)benzene (60 mL) was added N-bromosuccinimide (5.42 g), and the mixture was stirred at 80° C. overnight. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was 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 (hexane/ethyl acetate) to give the title compound (5.6 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-68b625bbc9744a11b14edfb1b1cbb6db
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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