1,4-Dibromobenzene → N-(3-(4-bromophenyl)oxetan-3-yl)-2-methylpropane-2-sulfinamide

HRID 624273Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][CH:3]=1.C([Li])CCC.[CH3:14][C:15]([S:18]([N:20]=[C:21]1[CH2:24][O:23][CH2:22]1)=[O:19])([CH3:17])[CH3:16].[Cl-].[NH4+]>O1CCCC1.ClCCl.O>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([C:21]2([NH:20][S:18]([C:15]([CH3:17])([CH3:16])[CH3:14])=[O:19])[CH2:24][O:23][CH2:22]2)=[CH:3][CH:4]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a 50 mL round-bottomed flask was added 1,4-dibromobenzene (2.85 g, 12.07 mmol) in tetrahydrofuran (40.2 ml). The solution was cooled to −78° C. and n-butyl lithium (4.51 ml, 11.26 mmol) was added dropwise. The mixture was stirred for 1 hour at −78° C. 2-methyl-N-(oxetan-3-ylidene)propane-2-sulfinamide (1.41 g, 8.05 mmol) was added as a tetrahydrofuran solution (ca 1 ml) and the reaction was stirred for 10 minutes and warmed to room temperature. Saturated ammonium chloride was added followed by water and dichloromethane. The aqueous layer was extracted twice with dichloromethane and the combined organics were dried with magnesium sulfate, filtered and concentrated under vacuum. The residue was purified by regular phase, flash column chromatography to give the title compound.

Workup

stirringthe reaction was stirred for 10 minutes
temperaturewarmed to room temperature
extractionThe aqueous layer was extracted twice with dichloromethane
dry with materialthe combined organics were dried with magnesium sulfate
filtrationfiltered
concentrationconcentrated under vacuum
customThe residue was purified by regular phase, flash column chromatography

Sources & evidence

ORD record: ord-da0af6dc42114bf2a8514e585f285db3
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09302989B2

Reaction notes

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