N-bromobutanimide → HCID 18992094, compound

HRID 375715Notes

Reaction equation

HRID 375715 reaction equation
[C:1]([O:4][C:5]1[C:6]([CH3:24])=[C:7]([C:16]([CH3:23])=[C:17]([O:19][C:20](=[O:22])[CH3:21])[CH:18]=1)[C:8]([O:10][CH2:11][C:12]([Cl:15])([Cl:14])[Cl:13])=[O:9])(=[O:3])[CH3:2].[Br:25]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[C:20]([O:19][C:17]1[C:16]([CH2:23][Br:25])=[C:7]([C:6]([CH3:24])=[C:5]([O:4][C:1](=[O:3])[CH3:2])[CH:18]=1)[C:8]([O:10][CH2:11][C:12]([Cl:14])([Cl:13])[Cl:15])=[O:9])(=[O:22])[CH3:21]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 18992074HCID 18992074, compound

Product 1

HCID 18992094HCID 18992094, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 4.76 g 2,2,2-trichloroethyl 3,5-diacetoxy-dimethylbenzoate and 2.24 g N-bromosuccinimide in 36 ml of carbontetrachloride was heated at reflux temperature and with light irradiation for 30 minutes. The mixture was cooled in an ice bath and insoluble material was removed by filtration. The filtrate was diluted with methylene chloride, washed with water, dried over sodium sulphate and evaporated in vacuo to provide crude 2,2,2-trichloroethyl 3,5-diacetoxy-2-bromomethyl-6-methylbenzoate, which was used directly without further purification.

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature
  3. customwith light irradiation for 30 minutes
  4. temperatureThe mixture was cooled in an ice bath
  5. custominsoluble material was removed by filtration
  6. additionThe filtrate was diluted with methylene chloride
  7. washwashed with water
  8. dry with materialdried over sodium sulphate
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-dc0bda722f4842899c84377c2eef0d05
Source dataset
uspto-grants-1996_01
Patent number
US05486466

Reaction notes

Loading…