Azobisisobutyronitrile → 2,6-Dichloro-3-nitrobenzyl Bromide

HRID 356099Notes

Reaction equation

HRID 356099 reaction equation
[Br:1]C1(Br)NC(=O)NC1=O.CC(N=NC(C#N)(C)C)(C#N)C.[Cl:22][C:23]1[C:28]([N+:29]([O-:31])=[O:30])=[CH:27][CH:26]=[C:25]([Cl:32])[C:24]=1[CH3:33].C(OCC)(=O)C>ClC1C=CC=CC=1>[Cl:22][C:23]1[C:28]([N+:29]([O-:31])=[O:30])=[CH:27][CH:26]=[C:25]([Cl:32])[C:24]=1[CH2:33][Br:1]

Participants

6

Reactant 4

HCID 6547Azobisisobutyronitrile2×HCID 8857Ethyl AcetateHCID 971552,6-Dichloro-3-nitrotolueneHCID 54068228Dibromohydantoin2×

Product 1

HCID 110115352,6-Dichloro-3-nitrobenzyl Bromide

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

A mixture of dibromohydantoin (70 g, 0.24 mol) and AIBN (5 g) was added in portions, at 150° C., to 2,6-dichloro-3-nitrotoluene (100 g, 0.48 mol) in chlorobenzene (400 ml). A mixture of dibromohydantoin (35 g, 0.12 mol) and AIBN (2.5 g) was added once again after 1 h. After a further 1.5 h, the mixture was allowed to cool down and ethyl acetate (500 ml) was added. This mixture was washed once, in each case, with saturated Na2SO3, Na2CO3 and NaCl solution, dried (MgSO4) and concentrated, when the title compound resulted as an amorphous powder. ##EQU1## b) 4-(2,6-Dichloro-3-nitrobenzyloxy)benzothiazole

Workup

  1. additionwas added once again after 1 h
  2. temperatureto cool down
  3. washThis mixture was washed once, in each case, with saturated Na2SO3, Na2CO3 and NaCl solution
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c67fcee6818b44f9bd1756eb14aa2056
Source dataset
uspto-grants-1998_11
Patent number
US05834500

Reaction notes

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