Chloroform → Thiophene, 3-(bromomethyl)-2,5-dihydro-, 1,1-dioxide

HRID 1462857

Reaction equation

HRID 1462857 reaction equation
[CH3:1][C:2]1[CH2:3][S:4]([CH2:7][CH:8]=1)(=[O:6])=[O:5].[Br:9]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C(Cl)(Cl)Cl>CCOCC>[Br:9][CH2:1][C:2]1[CH2:3][S:4]([CH2:7][CH:8]=1)(=[O:6])=[O:5]

Participants

6

Reactant 4

HCID 6212ChloroformHCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 70941Thiophene, 2,5-dihydro-3-methyl-, 1,1-dioxide

Product 1

HCID 712958Thiophene, 3-(bromomethyl)-2,5-dihydro-, 1,1-dioxideYield 34.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

In a reaction vessel, 21.0 gms (0.1591 moles) 3-methyl sulfolene, 28.32 gms (0.1591 moles) N-bromo succinimide, 1.9 gms (0.0008 moles) benzoyl peroxide and 250 ml chlorform were combined. The resulting mixture was heated to reflux and then refluxed for 20 hours. The reaction mixture was cooled to 0° C. and then filtered to remove the succinimide. The filtrate was stripped until only a small amount of solvent remained. The remaining solids were removed by filtration, and the remainder of the solvent was stripped to give an orange oil. Ether was added to the oil. After a few minutes, the solids crystallized. Filtration and drying yielded 11.5 gms of the product. The NMR and IR spectra confirmed the structure.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux
  3. temperaturerefluxed for 20 hours
  4. filtrationfiltered
  5. customto remove the succinimide
  6. customThe remaining solids were removed by filtration
  7. customto give an orange oil
  8. waitAfter a few minutes
  9. customthe solids crystallized
  10. filtrationFiltration
  11. customdrying

Sources & evidence

ORD record
ord-4ee0407e9047430eacd01aa33f279a11
Source dataset
uspto-grants-1984_07
Patent number
US04461764

Linked notes

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