N-bromobutanimide → HCID 13662981, compound

HRID 648022Notes

Reaction equation

HRID 648022 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:9][C:8]2[CH:10]=[CH:11][C:12]([CH3:14])=[CH:13][C:7]=2[CH:6]=1)=[O:4].[Br:15]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.N(C(C)(C)C#N)=NC(C)(C)C#N>[CH3:1][O:2][C:3]([C:5]1[S:9][C:8]2[CH:10]=[CH:11][C:12]([CH2:14][Br:15])=[CH:13][C:7]=2[CH:6]=1)=[O:4]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 13662971Methyl 5-methyl-1-benzothiophene-2-carboxylate

Product 1

HCID 13662981HCID 13662981, compoundYield 97.4%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 5-methylbenzo[b]thiophene-2-carboxylic acid methyl ester (3.09 g.), N-bromosuccinimide (2.67 g.) and azobisisobutyronitrile (0.20 g.) in carbon tetrachloride (150 ml.) was heated under reflux for 5 hours. The mixture was then filtered and the filtrate was evaporated to give a solid which was crystallized from methanol to give 5-bromomethylbenzo[b]thiophene-2-carboxylic acid methyl ester (4.16 g.), m.p. 108°-110°.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 5 hours
  3. filtrationThe mixture was then filtered
  4. customthe filtrate was evaporated
  5. customto give a solid which
  6. customwas crystallized from methanol

Sources & evidence

ORD record
ord-6184cf64deba45759ccb5b676b87db5d
Source dataset
uspto-grants-1983_10
Patent number
US04410539

Reaction notes

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