Ammonium nitrate → 4,4'-Dibromobenzil

HRID 1595953Notes

Reaction equation

HRID 1595953 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-3be651f63c564bb6a69fac902a16e708
Source dataset
uspto-grants-2001_09
Patent number
US06288188B1

Reaction notes

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