Benzoyl Peroxide → HCID 15744971, compound

HRID 327473Notes

Reaction equation

HRID 327473 reaction equation
[C:1]([N:4]([C:8]1[C:13]([CH3:14])=[CH:12][CH:11]=[CH:10][C:9]=1[O:15][CH3:16])[C:5](=[O:7])[CH3:6])(=[O:3])[CH3:2].[Br:17]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[C:1]([N:4]([C:8]1[C:9]([O:15][CH3:16])=[CH:10][CH:11]=[CH:12][C:13]=1[CH2:14][Br:17])[C:5](=[O:7])[CH3:6])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 15744970HCID 15744970, compound

Product 1

HCID 15744971HCID 15744971, compoundYield 63.6%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of N-acetyl-N-(2-methoxy-6-methylphenyl)acetamide (25.0 g, 0.11 mol), N-bromosuccinimide (20.1 g, 0.11 mol), and benzoyl peroxide (4.5 g, 0.019 mol) in carbon tetrachloride (300 mL) was stirred under reflux for 3 hours. The solution was cooled, filtered, and evaporated, and the residual solid was crystallized from ethyl acetate:hexane to give 21.0 g of N-acetyl-N-(2-(bromomethyl)-6-methoxyphenyl)acetamide, 95% pure by GC analysis.

Workup

  1. temperatureunder reflux for 3 hours
  2. temperatureThe solution was cooled
  3. filtrationfiltered
  4. customevaporated
  5. customthe residual solid was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-58a90fc7c8cf4185939f20ac84246216
Source dataset
uspto-grants-1993_12
Patent number
US05273975

Reaction notes

Loading…