Chloroform → HCID 44207525, compound

HRID 1949145Notes

Reaction equation

HRID 1949145 reaction equation
C(Cl)(Cl)Cl.[F:5][C:6]1[CH:7]=[C:8]([CH:12]2[C:16]([OH:17])=[C:15]([C:18]([CH3:20])=[O:19])[CH2:14][S:13]2)[CH:9]=[CH:10][CH:11]=1.S(Cl)(Cl)(=O)=O>O>[F:5][C:6]1[CH:7]=[C:8]([C:12]2[S:13][CH:14]=[C:15]([C:18]([CH3:20])=[O:19])[C:16]=2[OH:17])[CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 6212Chloroform2×HCID 24648Sulfuryl chlorideHCID 44207287HCID 44207287, compound

Product 1

HCID 44207525HCID 44207525, compoundYield 44.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A chloroform (6.2 mL) solution of 2-(3-fluorophenyl)-3-hydroxy-4-methylcarbonyl-2,5-dihydrothiophene (0.61 g, 2.58 mmol, purity: 78%) was cooled to −40° C., and to this solution, a chloroform (1.2 mL) solution of sulfuryl chloride (0.21 mL, 1.0 equivalent amount) was dropwise added over a period of 3 minutes. The temperature of the solution was raised to 0° C., and water (1.2 mL) was dropwise added over a period of 1 minute, followed by liquid separation. The obtained chloroform solution was sequentially washed with water, a saturated salt solution, a saturated sodium hydrogencarbonate aqueous solution, a saturated sodium thiosulfate aqueous solution and a saturated salt solution, and dried over anhydrous magnesium sulfate. The drying agent was removed by filtration, and the solvent was distilled off to obtain a crude product. The obtained crude product was isolated and purified by column chromatography (eluent: hexane/ethyl acetate=5/1 (v/v)) to give the desired product as a green solid (0.27 g, yield: 44%).

Workup

  1. customfollowed by liquid separation
  2. washThe obtained chloroform solution was sequentially washed with water
  3. dry with materiala saturated salt solution, a saturated sodium hydrogencarbonate aqueous solution, a saturated sodium thiosulfate aqueous solution and a saturated salt solution, and dried over anhydrous magnesium sulfate
  4. customThe drying agent was removed by filtration
  5. distillationthe solvent was distilled off
  6. customto obtain a crude product
  7. customThe obtained crude product
  8. customwas isolated
  9. custompurified by column chromatography (eluent: hexane/ethyl acetate=5/1 (v/v))

Sources & evidence

ORD record
ord-0609f3e3dd8c46258d5c9cdfd629fe53
Source dataset
uspto-grants-2013_03
Patent number
US08399685B2

Reaction notes

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