Bromide ion → HCID 58856298, compound

HRID 2055770Notes

Reaction equation

HRID 2055770 reaction equation
[Br-].[C:2](=[S:4])=[S:3].Br[CH:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:7]#[N:8].O>C1COCC1>[CH3:6][C:9]1[CH:14]=[CH:13][C:12]([C:2]([S:4][CH:6]([C:7]#[N:8])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[S:3])=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 259Bromide ionHCID 962WaterHCID 6348Carbon DisulfideHCID 22044Bromobenzyl Cyanide

Product 1

HCID 58856298HCID 58856298, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 100 ml round bottom flask was added 10 ml 4-tolylmagiesium bromide (1.0M solution in ethyl ether) and diluted to 20 ml with anhydrous THF. 0.76 g carbon disulfide was added dropwise to this mixture and stirred for ½ h at room temperature. Then to the dark red solution was added 2 g α-bromobenzeneacetonitrile dropwise and the mixture stirred for another 2 h. Water was added to the mixture and the organic product was extracted with diethyl ether (3×50 ml), dried with magnesium sulfate overnight and filtered. After removal of solvent and column chromatography (5:2 mixture of hexane and ethyl ether), pure α-cyanobenzyl 4-methyldithiobenzoate was obtained as a red odorless solid (48% yield). Proton and carbon NMR spectra were consistent with the expected structure, CTA-CP-6.

Workup

  1. stirringthe mixture stirred for another 2 h
  2. extractionthe organic product was extracted with diethyl ether (3×50 ml)
  3. dry with materialdried with magnesium sulfate overnight
  4. filtrationfiltered
  5. customAfter removal of solvent and column chromatography (5:2 mixture of hexane and ethyl ether)

Sources & evidence

ORD record
ord-418b1d1043f64bbeaf437f1b066bce05
Source dataset
uspto-grants-2008_02
Patent number
US07332552B2

Reaction notes

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