Water → 1-(5-(4-Bromophenyl)-4-hydroxythiophen-3-YL)ethan-1-one

HRID 239217Notes

Reaction equation

HRID 239217 reaction equation
C(Cl)(Cl)Cl.[Br:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]2[C:16]([OH:17])=[C:15]([C:18]([CH3:20])=[O:19])[CH2:14][S:13]2)=[CH:8][CH:7]=1.S(Cl)(Cl)(=O)=O.O>CC(O)C>[Br:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]2[S:13][CH:14]=[C:15]([C:18]([CH3:20])=[O:19])[C:16]=2[OH:17])=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6212Chloroform2×HCID 24648Sulfuryl chlorideHCID 44207042HCID 44207042, compound

Product 1

HCID 442072901-(5-(4-Bromophenyl)-4-hydroxythiophen-3-YL)ethan-1-oneYield 81.8%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
-20 °C

Procedure

A chloroform (249 mL) solution of 2-(4-bromophenyl)-3-hydroxy-4-methylcarbonyl-2,5-dihydrothiophene (24.9 g, 64.6 mmol, purity: 78%) was cooled to −23° C., and a chloroform (50 mL) solution of sulfuryl chloride (5.45 mL, 1.05 equivalent amounts) was dropwise added over a period of 27 minutes, followed by stirring at −20° C. for 1 hour. The temperature of the solution was raised to −5° C., and water (50 mL) was dropwise added over a period of 3 minutes, followed by liquid separation. The obtained chloroform solution was sequentially washed with water, a saturated salt solution, a sodium hydroxide 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. To the obtained crude product, 2-propanol (374 mL) was added, followed by stirring at 0° C. for 40 minutes. The formed crystals were removed by filtration to give the desired product as a yellow solid (15.7 g, yield: 63%).

Workup

  1. temperatureThe temperature of the solution was raised to −5° C.
  2. customfollowed by liquid separation
  3. washThe obtained chloroform solution was sequentially washed with water
  4. dry with materiala saturated salt solution, a sodium hydroxide aqueous solution, a saturated sodium thiosulfate aqueous solution and a saturated salt solution, and dried over anhydrous magnesium sulfate
  5. customThe drying agent was removed by filtration
  6. distillationthe solvent was distilled off
  7. customto obtain a crude product
  8. additionwas added
  9. stirringby stirring at 0° C. for 40 minutes
  10. customThe formed crystals were removed by filtration

Sources & evidence

ORD record
ord-f6147c3bcfd54e94868f71ee83efc6cf
Source dataset
uspto-grants-2014_02
Patent number
US08642786B2

Reaction notes

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