Ammonium nitrate → 4,4'-Dibromobenzil

HRID 1739361Notes

Reaction equation

HRID 1739361 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH:10]([C:12]2[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][CH:13]=2)[OH:11])=[O:9])=[CH:4][CH:3]=1.[N+]([O-])([O-])=O.[NH4+]>C(O)(=O)C.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:10]([C:12]2[CH:13]=[CH:14][C:15]([Br:18])=[CH:16][CH:17]=2)=[O:11])=[O:9])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 22985Ammonium nitrateHCID 39382434,4'-dibromobenzoin

Product 1

HCID 964304,4'-DibromobenzilYield 64.2%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 4,4'-dibromobenzoin (20.2 g, 0.055 mol), ammonium nitrate (4.6 g, 0.0575 mol) and copper(II) acetate (0.100 g, 0.0005 mol) in 80 percent aqueous acetic acid (200 mL) is heated at reflux for three hours. The reaction mixture is cooled to room temperature and the product which crystallizes out is filtered off, washed with ethanol and dried, giving 13.0 g (64 percent) of product as a light yellow solid, mp 226° C. to 228° C. 1H NMR (CDCl3) δ 7.83 (d, J=8.5 Hz, 4H), 7.66 (d, J=8.5 Hz, 4H); 13C NMR (CDCl3) δ 192.25, 132.44, 131.45, 131.22, 130.7.

Workup

  1. temperatureat reflux for three hours
  2. customthe product which crystallizes out
  3. filtrationis filtered off
  4. washwashed with ethanol
  5. customdried

Sources & evidence

ORD record
ord-4a898eebc49f413ca412af05344043c3
Source dataset
uspto-grants-1999_10
Patent number
US05965679

Reaction notes

Loading…