N-bromobutanimide → HCID 22282008, compound

HRID 1368668Notes

Reaction equation

HRID 1368668 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH3:9][O:10][C:11]1[CH:23]=[CH:22][CH:21]=[CH:20][C:12]=1[O:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16]>C(Cl)(Cl)(Cl)Cl>[Br:1][CH:14]([O:13][C:12]1[CH:20]=[CH:21][CH:22]=[CH:23][C:11]=1[O:10][CH3:9])[C:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 83114Ethyl (2-methoxyphenoxy)acetate

Product 1

HCID 22282008HCID 22282008, compoundYield 105.9%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of N-bromosuccinimide (13.35 g), azoisobutyronitrile (200 mg) and ethyl 2-(2-methoxyphenoxy)acetate (15.1 g) in anhydrous carbon tetrachloride (ex. calcium hydride) (100 ml) was irradiated with a 120 W sunlamp under reflux and a nitrogen atmosphere for 7 hours. The resulting suspension was allowed to stand at room temperature for 72 hours and was then filtered to remove the suspended solids, which were washed with toluene (40 ml). The combined filtrates were evaporated under vacuum leaving a brown liquid (22 g) Rf 0.75 (dichloromethane).

Workup

  1. temperatureunder reflux
  2. waitto stand at room temperature for 72 hours
  3. filtrationwas then filtered
  4. customto remove the suspended solids, which
  5. washwere washed with toluene (40 ml)
  6. customThe combined filtrates were evaporated under vacuum

Sources & evidence

ORD record
ord-2c8b4bb840e84db88511c7b5e5a24f84
Source dataset
uspto-grants-2003_06
Patent number
US06573270B1

Reaction notes

Loading…