Azobisisobutyronitrile → HCID 19098812, compound

HRID 1975827Notes

Reaction equation

HRID 1975827 reaction equation
[C:1]([O:9][C:10]1[C:11]([O:17][C:18](=[O:25])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:12][C:13]([CH3:16])=[CH:14][CH:15]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N(C(C)(C)C#N)=NC(C)(C)C#N.[Br:38]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[C:1]([O:9][C:10]1[C:11]([O:17][C:18](=[O:25])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:12][C:13]([CH2:16][Br:38])=[CH:14][CH:15]=1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 19098816HCID 19098816, compound

Product 1

HCID 19098812HCID 19098812, compoundYield 28.6%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 19.94 g (0.06 mol) of 4-methyl-benzene-1,2-diol dibenzoate in 350 mL of carbon tetrachloride was added a catalytic amount of 2,2'-azobisisobutyronitrile, followed by 10.68 g (0.06 mol) of N-bromosuccinimide. The reaction mixture was stirred at room temperature for several days and was then filtered. The filtrate was dried over MgSO4, filtered and evaporated to dryness in a rotary evaporator. Purification of the crude material (24.76 g) by HPLC gave 7.05 g of product which was used directly in the next step.

Workup

  1. filtrationwas then filtered
  2. dry with materialThe filtrate was dried over MgSO4
  3. filtrationfiltered
  4. customevaporated to dryness in a rotary evaporator
  5. customPurification of the crude material (24.76 g) by HPLC

Sources & evidence

ORD record
ord-d25ca221be4d4a16ab7ded46f8439474
Source dataset
uspto-grants-1994_02
Patent number
US05288871

Reaction notes

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