Benzyl Bromide → 1-(2-(Benzylthio)-5-chlorothiophen-3-yl)ethanone
Reaction equation
N[C:2](N)=[S:3].C(Br)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[C:13]([C:16]1[CH:20]=[C:19]([Cl:21])[S:18][C:17]=1Cl)(=[O:15])[CH3:14].[OH-].[Na+]>O.C1COCC1>[C:13]([C:16]1[CH:20]=[C:19]([Cl:21])[S:18][C:17]=1[S:3][CH2:2][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)(=[O:15])[CH3:14]Participants
Conditions
- Temperature
- 50 °C
Procedure
A mixture consisting of thiourea (858.4 g, 11.28 mol), benzyl bromide (1,930 g, 11.28 mol), THF (9000 ml), and water (3000 ml) was heated at reflux temperature for 2 hr followed by cooling to 50° C. To this solution was added 3-acetyl-2,5-dichlorothiophene (2000 g, 10.25 mol) and an aqueous solution of sodium hydroxide (2,200 g of 50% NaOH diluted to 3000 ml); this mixture was heated at reflux temperature for 4 hr, cooled to room temperature, and the two layers separated. The organic layer was diluted with ethyl acetate (6000 ml) and washed with water (3×2000 ml) and saturated aqueous sodium chloride, dried (MgSO4) and the solvent evaporated to give a residue which was triturated with hexane. This solid was collected by filtration and dried to give the desired product (2,550 g, 88%): mp 86°-88° C.
Workup
- temperaturewas heated
- temperatureat reflux temperature for 2 hr
- temperaturethis mixture was heated
- temperatureat reflux temperature for 4 hr
- temperaturecooled to room temperature
- customthe two layers separated
- additionThe organic layer was diluted with ethyl acetate (6000 ml)
- washwashed with water (3×2000 ml) and saturated aqueous sodium chloride
- dry with materialdried (MgSO4)
- customthe solvent evaporated
- customto give a residue which
- customwas triturated with hexane
- filtrationThis solid was collected by filtration
- customdried
Sources & evidence
- ORD record
- ord-2cba84e987644564911be898ff00151b
- Source dataset
- uspto-grants-1996_07
- Patent number
- US05538966
Reaction notes
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