Triethylamine → HCID 14275575, compound

HRID 867971Notes

Reaction equation

HRID 867971 reaction equation
Br[CH2:2][C:3]1[O:4][C:5](=[O:8])[O:6][CH:7]=1.[F:9][C:10]1[CH:15]=[CH:14][C:13]([SH:16])=[CH:12][CH:11]=1.C(N(CC)CC)C>ClCCl>[F:9][C:10]1[CH:15]=[CH:14][C:13]([S:16][CH2:2][C:3]2[O:4][C:5](=[O:8])[O:6][CH:7]=2)=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 677894-FluorothiophenolHCID 12832615HCID 12832615, compound

Product 1

HCID 14275575HCID 14275575, compoundYield 41.1%

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 0.8 g of 4-fluorobenzenethiol 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 insoluble materials were separated by filtration, and the solvent 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 evaporated under reduced pressure, and the residue was recrystallized from a mixture of ethyl acetate and n-hexane to give 0.52 g of the captioned compound as pale yellow crystals.

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 insoluble materials were separated by filtration
  6. customthe solvent was evaporated under reduced pressure
  7. washwas eluted with a mixture of chloroform and n-hexane (2/1
  8. customThe eluate was evaporated under reduced pressure
  9. customthe residue was recrystallized from a mixture of ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-955000c5669540dab8a108188393c24d
Source dataset
uspto-grants-1988_10
Patent number
US04777267

Reaction notes

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