N-bromobutanimide → Trimethylsilyl-4-bromocrotonate

HRID 714582Notes

Reaction equation

HRID 714582 reaction equation
[C:1]([O:6][Si:7]([CH3:10])([CH3:9])[CH3:8])(=[O:5])/[CH:2]=[CH:3]/[CH3:4].C1C(=O)N([Br:18])C(=O)C1>C(Cl)(Cl)(Cl)Cl>[Br:18][CH2:4]/[CH:3]=[CH:2]/[C:1]([O:6][Si:7]([CH3:10])([CH3:9])[CH3:8])=[O:5]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 5702560Trimethylsilyl crotonate

Product 1

HCID 12730183Trimethylsilyl-4-bromocrotonate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a single-neck reaction flask (250 mL) were added (E)-trimethylsilyl 2-butenoate (12.242 g, 77.481 mmol), NBS (16.550 g, 92.977 mmol), (PhCO2)2 (310 mg) and carbon tetrachloride (100 mL). The mixture was stirred under reflux for 3.5 hr. The resulting mixture was cooled in an ice-water bath. The insoluble substance was filtered. The residue was rotatory-evaporated and concentrated until no liquid dropped. The concentrate was distilled under reduced pressure to collect the fraction under 9 mmHg at the temperature of 100° C.-102° C. to give the target compound as a colorless transparent liquid.

Workup

  1. temperatureunder reflux for 3.5 hr
  2. temperatureThe resulting mixture was cooled in an ice-water bath
  3. filtrationThe insoluble substance was filtered
  4. customThe residue was rotatory-evaporated
  5. concentrationconcentrated until no liquid
  6. additiondropped
  7. distillationThe concentrate was distilled under reduced pressure
  8. customto collect the fraction under 9 mmHg at the temperature of 100° C.-102° C.

Sources & evidence

ORD record
ord-94f92db0cf43444f9e0aefc4ae807560
Source dataset
uspto-grants-2015_11
Patent number
US09187458B2

Reaction notes

Loading…