Chloroform → HCID 44207524, compound

HRID 1967600Notes

Reaction equation

C(Cl)(Cl)Cl.[F: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>[F: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

Conditions

Temperature: -11 °C

Procedure

A chloroform (6.3 mL) solution of 2-(4-fluorophenyl)-3-hydroxy-4-methylcarbonyl-2,5-dihydrothiophene (0.63 g, 2.38 mmol, purity: 90%) was cooled to −12° C., and to this solution, a chloroform (1.3 mL) solution of sulfuryl chloride (0.23 mL, 1.2 equivalent amounts) was dropwise added over a period of 6 minutes, followed by stirring at −11° C. for 2 hours. The temperature of the solution was raised to 3° C., and water (1.3 mL) was dropwise added, 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 give the desired product as a yellow solid (0.28 g, yield: 50%).

Workup

temperatureThe temperature of the solution was raised to 3° C.
customfollowed by liquid separation
washThe obtained chloroform solution was sequentially washed with water
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
customThe drying agent was removed by filtration
distillationthe solvent was distilled off

Sources & evidence

ORD record: ord-7fbe8d229b0841a38459620554245606
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08420849B2

Reaction notes

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