Bromocyclopropane → HCID 58392457, compound

HRID 561460Notes

Reaction equation

HRID 561460 reaction equation
[CH:1]1(Br)[CH2:3][CH2:2]1.[Mg].[F:6][C:7]1[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[CH:9][C:8]=1[C:17](=[O:19])[CH3:18]>BrC(Br)C.C(OCC)C>[CH:1]1([C:17]([C:8]2[CH:9]=[CH:10][C:11]([C:13]([F:14])([F:15])[F:16])=[CH:12][C:7]=2[F:6])([OH:19])[CH3:18])[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 78037BromocyclopropaneHCID 1455682-Fluoro-4-(trifluoromethyl)acetophenoneHCID 5462224Magnesium

Product 1

HCID 58392457HCID 58392457, compound

Reagents, catalysts & solvents 2

HCID 112011,1-DibromoethaneCatalystHCID 3283Diethyl EtherSolvent3×

Procedure

A few drops of dibromoethane and then 6.30 g (52.1 mmol) of cyclopropyl bromide, dissolved in 20 ml of diethyl ether, were added under argon to 1.33 g (54.7 mmol) of magnesium in 90 ml of dry diethyl ether. The mixture was heated under reflux for 2 h. After cooling, 21 ml (9.94 mmol) of the supernatant reaction solution were added dropwise under argon to a solution of 850 mg (4.12 mmol) of 1-[2-fluoro-4-(trifluoromethyl)phenyl]ethanone in 17 ml of diethyl ether, and the mixture was stirred at RT overnight. The reaction mixture was added to ice-water, the phases were separated, the aqueous phase was extracted with dichloromethane, and the combined organic phases were dried over magnesium sulfate, filtered and concentrated. The residue was purified by flash chromatography on silica gel (mobile phase: toluene/ethyl acetate gradient with addition of 0.1% triethylamine) to result in 157 mg (15% of theory) of a mixture of the diastereomers of the title compound.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 2 h
  3. temperatureAfter cooling
  4. customthe phases were separated
  5. extractionthe aqueous phase was extracted with dichloromethane
  6. dry with materialthe combined organic phases were dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by flash chromatography on silica gel (mobile phase: toluene/ethyl acetate gradient with addition of 0.1% triethylamine)

Sources & evidence

ORD record
ord-8929e21c93ea4f019bdc17dd3a6f1ac3
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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