Sulfuryl chloride → 4-(Oxan-4-yloxy)benzene-1-sulfonyl chloride

HRID 636936Notes

Reaction equation

Br[C:2]1[CH:14]=[CH:13][C:5]([O:6][CH:7]2[CH2:12][CH2:11][O:10][CH2:9][CH2:8]2)=[CH:4][CH:3]=1.C([Li])CCC.[S:20](Cl)([Cl:23])(=[O:22])=[O:21]>O1CCCC1.CCCCCC>[O:10]1[CH2:11][CH2:12][CH:7]([O:6][C:5]2[CH:13]=[CH:14][C:2]([S:20]([Cl:23])(=[O:22])=[O:21])=[CH:3][CH:4]=2)[CH2:8][CH2:9]1

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of 2.8 g of 4-(4-Bromo-phenoxy)-tetrahydropyran in 75 mL of dry tetrahydrofuran was added 7.5 mL of n-butyllithium (1.6 N in hexane) at −78° C. After stirring at −78° C. for 2 hours the reaction mixture was allowed to warm to −40° C. and a solution of 4.1 mL of sulfuryl chloride in 75 mL of dry hexane was added within 15 minutes. Stirring was continued for 1 hour at −30° C. and subsequently for another hour at 5° C. The mixture was poured on ice, extracted with diethyl ether and the ether extract washed with cold water and brine, dried (sodium sulfate), and concentrated. The residue was purified by silica chromatography (isohexane/ethyl acetate 4/1) yielding 0.62 g of 4-(tetrahydropyran-4-yloxy)-benzenesulfonyl chloride as a colorless oil. EI-MS: 276 (M+).

Workup

temperatureto warm to −40° C.
stirringStirring
waitwas continued for 1 hour at −30° C. and subsequently for another hour at 5° C
additionThe mixture was poured on ice
extractionextracted with diethyl ether
extractionthe ether extract
washwashed with cold water and brine
dry with materialdried (sodium sulfate)
concentrationconcentrated
customThe residue was purified by silica chromatography (isohexane/ethyl acetate 4/1)

Sources & evidence

ORD record: ord-5cd84e8770354989a2787d7e346be555
Source dataset: uspto-grants-2001_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06194409B1

Reaction notes

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