Carbon Disulfide → HCID 17866105, compound
Reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:8]([C:10]1[CH:17]=[CH:16][C:13]([CH2:14]Cl)=[CH:12][CH:11]=1)=[CH2:9].[C:18](=[S:20])=[S:19]>>[C:18]([S:20][CH2:14][C:13]1[CH:16]=[CH:17][C:10]([CH:8]=[CH2:9])=[CH:11][CH:12]=1)(=[S:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:8]([C:10]1[CH:17]=[CH:16][C:13]([CH2:14][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[C:18]([S-:20])=[S:19])=[CH:12][CH:11]=1)=[CH2:9]Participants
Conditions
- Temperature
- 50 °C
Procedure
4-vinylbenzyl dithiobenzoate (VBThB) was prepared according to reaction scheme 4, as follows. A 500 mL round bottom flask was dried with 3 vacuum/heat/nitrogen cycles. 100 mL of dry THF was added along with 3.3 grams of magnesium turnings. The mixture was placed in an oil bath set to 40° C., and 13.8 grams (0.088 moles) bromobenzene was added. 7.91 mL (0.088 moles) of dry carbon disulfide was added dropwise over the next 15 minutes. When all the carbon disulfide was added, the temperature was increased to 50° C., and 18.62 grams (0.088 moles) of 4-vinylbenzyl chloride was added. The solvent was removed. The crude product was purified via column chromatography over activated alumina (Brockman activity II). The final product was obtained as a red oil. The conversion was estimated at 48% after eluent removal.
Workup
- customaccording to reaction scheme 4
- customA 500 mL round bottom flask was dried with 3
- temperaturevacuum/heat/nitrogen cycles
- addition100 mL of dry THF was added along with 3.3 grams of magnesium turnings
- customThe mixture was placed in an oil bath
- customset to 40° C.
- customThe solvent was removed
- customThe crude product was purified via column chromatography over activated alumina (Brockman activity II)
Sources & evidence
- ORD record
- ord-63aa2bfd23c04708b1f47e88d539f1a5
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08883912B2
Reaction notes
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