Water → HCID 9899011, compound
Reaction equation
[CH3:1][Mg]Cl.[C:4](=[S:6])=[S:5].[CH2:7](Br)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O>C1COCC1>[C:4]([S:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)(=[S:5])[CH3:1]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 40 °C
Procedure
Methyl magnesium chloride (10 mL, 3M solution in THF) was diluted with THF (10 mL) and the resulting solution warmed to 40° C. Carbon disulfide (2.28 g, 0.03 mol) was added over 10 minutes while maintaining the reaction temperature at 40° C. The reaction was cooled to room temperature before adding benzyl bromide (5.1 g, 0.03 mol) over 15 minutes. The reaction temperature was increased to 50° C. and maintained for a further 45 minutes. Water (100 mL) was added and the organic products extracted with n-hexane (3×60 mL). The combined organic extracts were washed with water, brine and dried over anhydrous magnesium sulfate. After removal of solvent and column chromatography (Kieselgel-60, 70-230 mesh, 5% diethyl ether in n-hexane eluent), pure benzyl dithioacetate was obtained as a golden oil (3 g, 55% yield). 1H-nmr (CDCl3) d(ppm): 2.90 (s, 3H); 4.46 (s, 2H) and 7.31 (m, 5H).
Workup
- temperaturewhile maintaining the reaction temperature at 40° C
- temperatureThe reaction was cooled to room temperature
- temperatureThe reaction temperature was increased to 50° C.
- temperaturemaintained for a further 45 minutes
- extractionthe organic products extracted with n-hexane (3×60 mL)
- washThe combined organic extracts were washed with water, brine
- dry with materialdried over anhydrous magnesium sulfate
- customAfter removal of solvent and column chromatography (Kieselgel-60, 70-230 mesh, 5% diethyl ether in n-hexane eluent)
Sources & evidence
- ORD record
- ord-c24c15554cbc45acbe15655b1a64b230
- Source dataset
- uspto-grants-2007_07
- Patent number
- US07250479B2
Reaction notes
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