Benzoyl Peroxide → 2-Chloro-4-fluoro-5-diacetylaminobenzyl bromide

HRID 231436Notes

Reaction equation

HRID 231436 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([N:9]([C:13](=[O:15])[CH3:14])[C:10](=[O:12])[CH3:11])=[CH:4][C:3]=1[CH3:16].[Br:17]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([N:9]([C:13](=[O:15])[CH3:14])[C:10](=[O:12])[CH3:11])=[CH:4][C:3]=1[CH2:16][Br:17]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 200323702-Chloro-4-fluoro-5-diacetylaminotoluene

Product 1

HCID 200323672-Chloro-4-fluoro-5-diacetylaminobenzyl bromideYield 7.9%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 7.8 g (0.032 mole) of 2-chloro-4-fluoro-5-diacetylaminotoluene, 6.2 g (0.035 mole) of N-bromosuccinimide, 0.5 g of benzoyl peroxide, and 200 ml of carbon tetrachloride was heated at reflux for two days. This mixture was filtered, and the filtrate was washed with water. The filtrate was dried, and the solvent was evaporated under reduced pressure. The residue was passed through a column of silica gel, eluting with ethyl acetate/heptane (1/4). Appropriate fractions were combined, and the solvent was evaporated under reduced pressure, yielding 0.82 g of 2-chloro-4-fluoro-5-diacetylaminobenzyl bromide. The nmr was consistent with the proposed structure.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for two days
  3. filtrationThis mixture was filtered
  4. washthe filtrate was washed with water
  5. customThe filtrate was dried
  6. customthe solvent was evaporated under reduced pressure
  7. washeluting with ethyl acetate/heptane (1/4)
  8. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-af7bd7184ea249b885311bb03f4c861a
Source dataset
uspto-grants-1989_07
Patent number
US04846882

Reaction notes

Loading…