N-bromobutanimide → HCID 13037877, compound

HRID 2309742Notes

Reaction equation

HRID 2309742 reaction equation
[CH2:1]([C:8]1[C:9](=[O:13])[CH2:10][CH2:11][CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.BrN1C(=[O:20])CCC1=O>C(Cl)(Cl)(Cl)Cl>[CH2:1]([C:8]1[C:9](=[O:13])[CH2:10][CH:11]([OH:20])[CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 11378770HCID 11378770, compound

Product 1

HCID 13037877HCID 13037877, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 2-benzylcyclopent-2-en-1-one and N-bromosuccinimide in dry carbon tetrachloride (150 ml) is refluxed for 1 hour, cooled and filtered. The filtrate is concentrated under reduced pressure to approx. 100 ml, and mixed with a stirred suspension of silver acetate (5 g) in acetic acid (150 ml). The resulting mixture is heated to 50° C. for 30 minutes and then stirred at room temperature overnight. The mixture is filtered, poured onto H2O (50 ml) and extracted with methylene chloride (150 ml×3). The combined extracts are washed with water ag. sodium bicarbonate, ag. sodium chloride, dried and concentrated under reduced pressure. (b.pt. is 128°-132° at 0.05 mmHg). The crude acetate is added to a solution of KOH (1.1 g) in 10% aqueous MeOH (100 ml) and stirred at room temperature for 40 minutes, poured onto dil.HCl and extracted with Et20 (×3). The combined extracts are washed with water dried, concentrated under reduced pressure and finally distilled. The ketone has b.pt 150°-154° C. at 0.04 mmHg and nD 1.5562.

Workup

  1. temperatureis refluxed for 1 hour
  2. temperaturecooled
  3. filtrationfiltered
  4. concentrationThe filtrate is concentrated under reduced pressure to approx. 100 ml
  5. additionmixed with a stirred suspension of silver acetate (5 g) in acetic acid (150 ml)
  6. filtrationThe mixture is filtered
  7. additionpoured onto H2O (50 ml)
  8. extractionextracted with methylene chloride (150 ml×3)
  9. washThe combined extracts are washed with water ag
  10. dry with materialsodium chloride, dried
  11. concentrationconcentrated under reduced pressure
  12. additionThe crude acetate is added to a solution of KOH (1.1 g) in 10% aqueous MeOH (100 ml)
  13. stirringstirred at room temperature for 40 minutes
  14. additionpoured onto dil
  15. extractionHCl and extracted with Et20 (×3)
  16. washThe combined extracts are washed with water
  17. customdried
  18. concentrationconcentrated under reduced pressure
  19. distillationfinally distilled
  20. customhas b.pt 150°-154° C. at 0.04 mmHg and nD 1.5562

Sources & evidence

ORD record
ord-be7ca3465c3f484fa230f39025d2015b
Source dataset
uspto-grants-1987_09
Patent number
US04696944

Reaction notes

Loading…