N-bromobutanimide → HCID 11339960, compound

HRID 1776057Notes

Reaction equation

HRID 1776057 reaction equation
[I:1][C:2]1[S:3][C:4]([C:7]2[S:8][C:9]([C:12]3[S:13][CH:14]=[CH:15][CH:16]=3)=[CH:10][CH:11]=2)=[CH:5][CH:6]=1.[Br:17]N1C(=O)CCC1=O>CO>[I:1][C:2]1[S:3][C:4]([C:7]2[S:8][C:9]([C:12]3[S:13][C:14]([Br:17])=[CH:15][CH:16]=3)=[CH:10][CH:11]=2)=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 1843122,2':5',2''-Terthiophene, 5-iodo-

Product 1

HCID 11339960HCID 11339960, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

100 mg (0.27 mmol) of 2-iodo(5,2′:5′,2″-terthiophene) (1) obtained above in the first step of example 1 were diluted in 100 ml of methanol at 0° C. 2 equivalents of N-bromosuccinimide (NBS, 95 mg, 0.53 mmol) were then added. The mixture was left stirring, in the dark for 12 h. The solvent was then evaporated under reduced pressure. The crude product of the reaction was then purified by column chromatography using, as eluent, petroleum ether then a petroleum ether/dichloromethane (5/1: v/v) mixture. The expected product was isolated in the form of a yellow powder (115 mg; yield=95%).

Workup

  1. waitThe mixture was left
  2. customThe solvent was then evaporated under reduced pressure
  3. customThe crude product of the reaction was then purified by column chromatography

Sources & evidence

ORD record
ord-17e3e6d7d62d4d2cbd1f3e199ce4def1
Source dataset
uspto-grants-2016_02
Patent number
US09263683B2

Reaction notes

Loading…