N-bromobutanimide → alpha-Bromo-m-tolyl cyclopropyl ketone

HRID 436931Notes

Reaction equation

HRID 436931 reaction equation
[C:1]1([CH3:12])[CH:6]=[CH:5][CH:4]=[C:3]([C:7]([CH:9]2[CH2:11][CH2:10]2)=[O:8])[CH:2]=1.[Br:13]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[CH:9]1([C:7]([C:3]2[CH:2]=[C:1]([CH2:12][Br:13])[CH:6]=[CH:5][CH:4]=2)=[O:8])[CH2:10][CH2:11]1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 21431776Cyclopropyl 3-methylphenyl ketone

Product 1

HCID 21431784alpha-Bromo-m-tolyl cyclopropyl ketone

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A stirred suspension of cyclopropyl m-tolyl ketone (16 g) and N-bromosuccinimide (17.8 g) in carbon tetrachloride (100 ml) was irradiated and heated under reflux by means of a tungsten lamp for 2 hours and cooled. The solid was filtered off and the filtrate evaporated. The residual oil was distilled under reduced pressure and the fraction distilling at 115°-130°/0.1 mm was collected.

Workup

  1. customwas irradiated
  2. temperatureheated
  3. temperatureunder reflux by means of a tungsten lamp for 2 hours
  4. temperaturecooled
  5. filtrationThe solid was filtered off
  6. customthe filtrate evaporated
  7. distillationThe residual oil was distilled under reduced pressure
  8. distillationthe fraction distilling at 115°-130°/0.1 mm
  9. customwas collected

Sources & evidence

ORD record
ord-9d51acc89387497e886315db9019f4f1
Source dataset
uspto-grants-1977_06
Patent number
US04028404

Reaction notes

Loading…