Dibromomethane → 1-(3-Bromo-phenyl)-2-[1,3]dithietan-2-ylidene-2-pyridin-4-yl-ethanone

HRID 38066

Reaction equation

HRID 38066 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8](=[O:16])[CH2:9][C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)[CH:5]=[CH:6][CH:7]=1.BrCBr.[C:20](=[S:22])=[S:21].[C:23]([O-])([O-])=O.[K+].[K+]>CS(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([C:8](=[O:16])[C:9](=[C:20]2[S:22][CH2:23][S:21]2)[C:10]2[CH:11]=[CH:12][N:13]=[CH:14][CH:15]=2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 3024DibromomethaneHCID 6348Carbon DisulfideHCID 11430Potassium CarbonateHCID 539524231-(3-Bromophenyl)-2-(pyridin-4-yl)ethan-1-one

Product 1

HCID 154859131-(3-Bromo-phenyl)-2-[1,3]dithietan-2-ylidene-2-pyridin-4-yl-ethanoneYield 74%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

1-(3-Bromo-phenyl)-2-pyridin-4-yl-ethanone (150 mg, 0.54 mmol), dibromomethane (114 ul, 1.62 mmol) and carbon disulfide (77 ul, 1.62 mmol) were reacted at room temperature in dry DMSO in the presence of K2CO3 (225 mg, 1.62 mmol) for three hours. The reaction, evaporated to dryness, was worked up with water and ethyl acetate. The pooled organic extracts were washed with brine, dried over sodium sulphate and evaporated down. The crude material was purified by a quick elution with ethyl acetate through a pad of silica to give the clean product in 74% yield.

Workup

  1. customThe reaction
  2. customevaporated to dryness
  3. washThe pooled organic extracts were washed with brine
  4. dry with materialdried over sodium sulphate
  5. customevaporated down
  6. customThe crude material was purified by a quick elution with ethyl acetate through a pad of silica
  7. customto give the clean product in 74% yield

Sources & evidence

ORD record
ord-9d9771a2591945309c5b19668224ff47
Source dataset
uspto-grants-2013_09
Patent number
US08524707B2

Linked notes

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