Azobisisobutyronitrile → HCID 54207325, compound

HRID 280590Notes

Reaction equation

HRID 280590 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]2[C:12]([CH3:13])=[CH:11][S:10][C:9]=2[CH:14]=1)=[O:4].[Br:15]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]2[C:12]([CH2:13][Br:15])=[CH:11][S:10][C:9]=2[CH:14]=1)=[O:4]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 54127717HCID 54127717, compound

Product 1

HCID 54207325HCID 54207325, compoundYield 56.2%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 3-methylbenzo[b]thiophene-6-carboxylic acid methyl ester (1.03 g), N-bromosuccinimide (0.89 g), azobisisobutyronitrile (0.2 g) and carbon tetrachloride (25 ml) was heated under reflux for 2 hours and then cooled. The mixture was diluted with a few ml. of chloroform, washed with water, dried (Na2SO4) and evaporated to give a solid which was crystallized from ethyl acetate/petrol (b.p. 60°-80° C.) to give 3-bromomethylbenzo[b]thiophene-6-carboxylic acid methyl ester (0.80 g), m.p. 108°-110° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. temperaturecooled
  4. additionThe mixture was diluted with a few ml
  5. washof chloroform, washed with water
  6. dry with materialdried (Na2SO4)
  7. customevaporated
  8. customto give a solid which
  9. customwas crystallized from ethyl acetate/petrol (b.p. 60°-80° C.)

Sources & evidence

ORD record
ord-537cd57023d341c8a204ac72798c22dc
Source dataset
uspto-grants-1986_05
Patent number
US04590200

Reaction notes

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