Chloroform → HCID 44207523, compound

HRID 1967599Notes

Reaction equation

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

Participants

Conditions

Temperature: -25 °C

Procedure

A chloroform (3 mL) solution of 2-(2,4-dichlorophenyl)-3-hydroxy-4-methylcarbonyl-2,5-dihydrothiophene (0.3 g, 0.93 mmol, purity: 90%) was cooled to −36° C., and to this solution, a chloroform (5 mL) solution of sulfuryl chloride (0.082 mL, 1.2 equivalent amounts) was dropwise added over a period of 10 minutes, followed by stirring at −25° C. for 40 minutes. The temperature of the solution was raised to 5° C., and water (0.6 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 (0.27 g, yield: 91%).

Workup

temperatureThe temperature of the solution was raised to 5° 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-9258fa7c36104f4d9c06f0cc37401d19
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08420849B2

Reaction notes

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