Thiophenol → HCID 14275576, compound

HRID 867972Notes

Reaction equation

HRID 867972 reaction equation
Br[CH2:2][C:3]1[O:4][C:5](=[O:8])[O:6][CH:7]=1.[C:9]1([SH:15])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(N(CC)CC)C>ClCCl>[C:9]1([S:15][CH2:2][C:3]2[O:4][C:5](=[O:8])[O:6][CH:7]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 8471TriethylamineHCID 12832615HCID 12832615, compound

Product 1

HCID 14275576HCID 14275576, compoundYield 60.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 30 ml of dichloromethane was dissolved 1.0 g of 4-bromomethyl-1,3-dioxol-2-one, and 0.7 g of benzenethiol was added. Then, 0.6 g of triethylamine was added, and the mixture was stirred at room temperature for 1 hour. After the reaction, the solvent was evaporated under reduced pressure. The residue was dissolved in ethyl acetate. The isoluble materials were separated by filtration, and the residue was evaporated under reduced pressure. The residue was subjected to medium-pressure silica gel column chromatography as in Example 1 except that the column was eluted with a mixture of chloroform and n-hexane (2/1, v/v). The eluate was concentrated under reduced pressure to give 0.7 g of the captioned compound as a colorless liquid.

Workup

  1. additionwas added
  2. customAfter the reaction
  3. customthe solvent was evaporated under reduced pressure
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. customThe isoluble materials were separated by filtration
  6. customthe residue was evaporated under reduced pressure
  7. washwas eluted with a mixture of chloroform and n-hexane (2/1
  8. concentrationThe eluate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-8563285316e54b12bcc699dcc5b285e2
Source dataset
uspto-grants-1988_10
Patent number
US04777267

Reaction notes

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