Potassium thiocyanate → (2-Bromo-4,6-dinitro-phenyl) thiocyanate

HRID 712156Notes

Reaction equation

HRID 712156 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([N+:11]([O-:13])=[O:12])[C:3]=1Br.[S-:15][C:16]#[N:17].[K+]>CO>[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([N+:11]([O-:13])=[O:12])[C:3]=1[S:15][C:16]#[N:17]

Participants

4

Reactant 2

HCID 516872Potassium thiocyanateHCID 12244454Benzene, 1,2-dibromo-3,5-dinitro-

Product 1

HCID 86663954(2-Bromo-4,6-dinitro-phenyl) thiocyanateYield 81.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 1,2-dibromo-3,5-dinitrobenzene (723 g, 2.22 mol) in MeOH (7.5 L) at rt was added potassium thiocyanate (431 g, 4.44 mol) and the resulting reaction mixture stirred under a nitrogen atmosphere for 16 h. The reaction mixture was then filtered and washed with methanol. The filtrate was concentrated at 30-33° C. under reduced pressure. The residue thus obtained was purified over silica gel (2-6% EtOAc-hexane) to obtain the desired product (549 g, 81%).

Workup

  1. customthe resulting reaction mixture
  2. filtrationThe reaction mixture was then filtered
  3. washwashed with methanol
  4. concentrationThe filtrate was concentrated at 30-33° C. under reduced pressure
  5. customThe residue thus obtained
  6. customwas purified over silica gel (2-6% EtOAc-hexane)

Sources & evidence

ORD record
ord-b25ab365dbe545558558fe4e0fff602f
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

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