N-bromobutanimide → HCID 20205050, compound

HRID 978096Notes

Reaction equation

HRID 978096 reaction equation
[CH3:1][C:2]1[S:6][C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[C:3]=1[O:11][C:12](=[O:14])[CH3:13].[Br:15]N1C(=O)CCC1=O>C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:15][CH2:1][C:2]1[S:6][C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[C:3]=1[O:11][C:12](=[O:14])[CH3:13]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 12330804HCID 12330804, compound

Product 1

HCID 20205050HCID 20205050, compoundYield 102.7%

Reagents, catalysts & solvents 1

HCID 7187Benzoyl PeroxideCatalyst

Procedure

A suspension of 1.00 g (4.85 mmol) of 2-methyl-3-acetoxybenzo[b]thiophene, 1.21 g (6.78 mmol) of N-bromosuccinimide, and 10 mg benzoylperoxide was heated under reflux for 3 hours. The mixture was filtered and the filtrate was concentrated to afford 1.42 g (100%) of a pale yellow oil. NMR (CDCl3, 90 MHz) δ2.35 (s, 3H, OAc), 4.48 (s, 2H, --CH2 --Br), 7.2-7.8 (m, 4H).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hours
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-9f658b82f41145899ebfa5b68541921b
Source dataset
uspto-grants-1987_05
Patent number
US04663344

Reaction notes

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