2-Biphenylol, 3,5-dinitro- → 2-Chloro-3,5-dinitro-1,1'-biphenyl

HRID 442227Notes

Reaction equation

HRID 442227 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[C:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:5]=1O)([O-:3])=[O:2].P(Cl)(Cl)([Cl:22])=O>CN(C)C=O>[Cl:22][C:5]1[C:4]([N+:1]([O-:3])=[O:2])=[CH:9][C:8]([N+:10]([O-:12])=[O:11])=[CH:7][C:6]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 129002-Biphenylol, 3,5-dinitro-HCID 24813Phosphorus oxychloride

Product 1

HCID 214168092-Chloro-3,5-dinitro-1,1'-biphenyl

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 30.00 g. of 3,5-dinitro-2-biphenylol, 15 ml. of dimethylformamide, and 113 ml. of phosphorous oxychloride is heated on a steam bath for 2.25 hours. The mixture is then cooled to room temperature and poured slowly into approximately 600 g. of crushed ice. The precipitate that forms is isolated by filtration and washed with water. The solid is dissolved in chloroform and the chloroform solution is washed several times with 10% Na2CO3 and once with water. The chloroform solution is dried over MgSO4 and concentrated. The product is recrystallized from benzenehexane to give 19.07 g. of material (melting at 119°-20° ).

Workup

  1. additionA mixture of 30.00 g
  2. additionpoured slowly into approximately 600 g
  3. customThe precipitate that forms is isolated by filtration
  4. washwashed with water
  5. dissolutionThe solid is dissolved in chloroform
  6. washthe chloroform solution is washed several times with 10% Na2CO3
  7. dry with materialThe chloroform solution is dried over MgSO4
  8. concentrationconcentrated
  9. customThe product is recrystallized from benzenehexane
  10. customto give 19.07 g

Sources & evidence

ORD record
ord-138cd17cdbfc42d78cae9168abf83b51
Source dataset
uspto-grants-1977_08
Patent number
US04044148

Reaction notes

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