Chloroform → 1-{4-Hydroxy-5-[4-(trifluoromethyl)phenyl]thiophen-3-yl}ethan-1-one

HRID 1967595Notes

Reaction equation

HRID 1967595 reaction equation
C(Cl)(Cl)Cl.[F:5][C:6]([F:23])([F:22])[C:7]1[CH:12]=[CH:11][C:10]([CH:13]2[C:17]([OH:18])=[C:16]([C:19]([CH3:21])=[O:20])[CH2:15][S:14]2)=[CH:9][CH:8]=1.S(Cl)(Cl)(=O)=O>O>[F:22][C:6]([F:5])([F:23])[C:7]1[CH:8]=[CH:9][C:10]([C:13]2[S:14][CH:15]=[C:16]([C:19]([CH3:21])=[O:20])[C:17]=2[OH:18])=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 6212Chloroform2×HCID 24648Sulfuryl chlorideHCID 67159859HCID 67159859, compound

Product 1

HCID 602067891-{4-Hydroxy-5-[4-(trifluoromethyl)phenyl]thiophen-3-yl}ethan-1-oneYield 74.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
-4 °C

Procedure

A chloroform (223 mL) solution of 2-(4-trifluoromethylphenyl)-3-hydroxy-4-methylcarbonyl-2,5-dihydrothiophene (22.25 g, 69.46 mmol, purity: 90%) was cooled to −46° C., and to this solution, a chloroform (334 mL) solution of sulfuryl chloride (6.70 mL, 1.2 equivalent amounts) was dropwise added over a period of 10 minutes, followed by stirring at −4° C. for 10 minutes. The temperature of the solution was raised to 0° C., and water (45 mL) was dropwise added thereto over a period of 15 minutes, 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 silica gel column chromatography (eluent: hexane/chloroform=1/1 (v/v)) to give the desired product as a yellow solid (14.78 g, yield: 69%).

Workup

  1. temperatureThe temperature of the solution was raised to 0° C.
  2. waitover a period of 15 minutes
  3. customfollowed by liquid separation
  4. washThe obtained chloroform solution was sequentially washed with water
  5. 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
  6. customThe drying agent was removed by filtration
  7. distillationthe solvent was distilled off
  8. customto obtain a crude product
  9. customThe obtained crude product
  10. customwas isolated
  11. custompurified by silica gel column chromatography (eluent: hexane/chloroform=1/1 (v/v))

Sources & evidence

ORD record
ord-77ca294809ea49938a694f7955f4f101
Source dataset
uspto-grants-2013_04
Patent number
US08420849B2

Reaction notes

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