N-bromobutanimide → HCID 59715367, compound

HRID 2223321Notes

Reaction equation

HRID 2223321 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]([CH3:11])[C:5]2[S:6][CH:7]=[CH:8][C:4]=2[CH:3]=1.C1C(=O)N([Br:19])C(=O)C1>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:1][C:2]1[CH:10]=[C:9]([CH2:11][Br:19])[C:5]2[S:6][CH:7]=[CH:8][C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 597153795-Bromo-7-methylbenzo[b]thiophene

Product 1

HCID 59715367HCID 59715367, compoundYield 51.1%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
0 °C

Procedure

The thiophene (10.16 g, 1.0 equiv), NBS (8.76 g, 1.1 equiv), and benzoyl peroxide (0.54 g, 0.05 equiv) were dissolved in CCl4, heated to reflux under UV irradiation for 2 hr and then cooled to 0° C. and filtered. The filtrate was evaporated. Repeated trituration with hexane gave 5-bromo-7-bromomethyl-benzo[b]thiophene (7.0 g). Concentration of the hexane gave an oil which was purified by column chromatography (SiO2, hexane) to give additional product (total yield 9.96 g, 86%).

Workup

  1. temperatureheated
  2. temperatureto reflux under UV irradiation for 2 hr
  3. filtrationfiltered
  4. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-751925aeb4cf4a229bb2740c7b8be0fb
Source dataset
uspto-grants-2008_05
Patent number
US07375125B2

Reaction notes

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