p-Bromoacetophenone → 4-Bromo-1-(1,3-dithian-2-yl)ethylbenzene

HRID 2256566Notes

Reaction equation

HRID 2256566 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH3:9])=[CH:4][CH:3]=1.[CH2:11]([SH:15])[CH2:12][CH2:13][SH:14].B(F)(F)F.[CH3:20]COCC>ClC(Cl)Cl.ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH:9]2[S:15][CH2:11][CH2:12][CH2:13][S:14]2)[CH3:20])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 7466p-BromoacetophenoneHCID 8000Boron trifluoride etherateHCID 80131,3-Propanedithiol

Product 1

HCID 219601124-Bromo-1-(1,3-dithian-2-yl)ethylbenzene

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To the compound p-bromoacetophenone (36.85 g, 185 mmol) in trichloromethane (300 ml) was added 1,3-propanedithiol (25 g, 230 mmol) and boron trifluoride etherate (3 ml). The resulting mixture was stirred at room temperature for 48 hours. The mixture was diluted with dichloromethane (500 ml), washed twice with 10% sodium hydroxide (200 ml), water, and brine, and then dried (Na2SO4). The product was concentrated to an oil. A portion was stirred with ether (100 ml) and a crystalline product was formed. The crystalline product was recovered by filtration and purified by recrystallization to yield 4-bromo-1-(1,3-dithian-2-yl)ethylbenzene.

Workup

  1. washwashed twice with 10% sodium hydroxide (200 ml), water, and brine
  2. dry with materialdried (Na2SO4)
  3. concentrationThe product was concentrated to an oil
  4. stirringA portion was stirred with ether (100 ml)
  5. customa crystalline product was formed
  6. filtrationThe crystalline product was recovered by filtration
  7. custompurified by recrystallization

Sources & evidence

ORD record
ord-e97ed1e16a67434ab8cc09df57708d1f
Source dataset
uspto-grants-1997_08
Patent number
US05654319

Reaction notes

Loading…