N-bromobutanimide → HCID 22612209, compound

HRID 844015Notes

Reaction equation

HRID 844015 reaction equation
[Cl:1][C:2]1[CH:6]=[C:5]([Cl:7])[S:4][C:3]=1[CH3:8].C1C(=O)N([Br:16])C(=O)C1>C(Cl)(Cl)(Cl)Cl.CCCCCC.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:16][CH2:8][C:3]1[S:4][C:5]([Cl:7])=[CH:6][C:2]=1[Cl:1]

Participants

6

Reactant 2

HCID 67184N-bromobutanimideHCID 128752653,5-Dichloro-2-methylthiophene

Product 1

HCID 22612209HCID 22612209, compoundYield 55.3%

Reagents, catalysts & solvents 3

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolventHCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 3,5-Dichloro-2-methyl-thiophene (1.3 grams, 7.8 mmole), NBS (1.4 grams, 7.8 mmole) and benzoyl peroxide (0.065 g) in carbon tetrachloride (40 ml) was refluxed for 18 hours. The mixture was cooled to 0° C., diluted with 40 ml hexane and filtered. The filtrate was concentrated to an oil which was purified via flash chromatography on silica using hexane as eluent to give an oil (1.06 g). MW 245.95; MS (m/e) 246 (M++1).

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated to an oil which
  3. customwas purified via flash chromatography on silica

Sources & evidence

ORD record
ord-bbdb5362085947d6a1a13b12be82f353
Source dataset
uspto-grants-2002_04
Patent number
US06380218B1

Reaction notes

Loading…