Water → HCID 58856296, compound

HRID 2055769Notes

Reaction equation

HRID 2055769 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([Mg]Br)=[CH:4][CH:3]=1.[C:10](=[S:12])=[S:11].Br[CH:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:15]#[N:16].O>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:10]([S:12][CH:14]([C:15]#[N:16])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[S:11])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6348Carbon DisulfideHCID 22044Bromobenzyl CyanideHCID 178418676HCID 178418676, compound

Product 1

HCID 58856296HCID 58856296, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 100 ml round bottom flask was added 10 ml 4-fluorophenyl magnesium 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 (10:3 mixture of hexane and ethyl ether), pure α-cyanobenzyl 4-fluorodithiobenzoate was obtained as a red odorless solid (62% yield). Proton and carbon NMR spectra were consistent with the expected structure, CTA-CP-4.

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 (10:3 mixture of hexane and ethyl ether)

Sources & evidence

ORD record
ord-fa737985c53a4e2597b11fdd4e1537cb
Source dataset
uspto-grants-2008_02
Patent number
US07332552B2

Reaction notes

Loading…