Azobisisobutyronitrile → (1-Bromo-2-oxopropyl) oxybenzene

HRID 1982548

Reaction equation

HRID 1982548 reaction equation
[O:1]([CH2:8][C:9](=[O:11])[CH3:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:12]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>ClC(Cl)(Cl)Cl>[Br:12][CH:8]([O:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:9](=[O:11])[CH3:10]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 693131-Phenoxy-2-propanone

Product 1

HCID 20161336(1-Bromo-2-oxopropyl) oxybenzene

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

Phenoxy-2-propanone (0.10 mol), N-bromosuccinimide (0.10 mol) and a catalytic amount of 2,2'-azobis(2-methylpropionitrile) were stirred together in tetrachloromethane (100 ml) at 80° C. for 61/2 hours. The solvent was distilled off and the residue distilled under vacuum to give (1-bromo-2-oxopropyl) oxybenzene. Yield: 10.4 g (45%), b.p. 66°-68° C./0.01 mm Hg. 1H NMR (CDCl3, δ): 2.50 (s, CH3) 6.40 (s, --CHBr--), 6.9-7.5 (5H, Ph).

Workup

  1. distillationThe solvent was distilled off
  2. distillationthe residue distilled under vacuum

Sources & evidence

ORD record
ord-14f1c6fd78234849a932491a3d8d0b3e
Source dataset
uspto-grants-1986_06
Patent number
US04596870

Linked notes

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