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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1023307Generated: October 31, 2026

1,4-Dibromobenzene → 4-(4-Bromophenyl)-1lambda~6~,4-thiazinane-1,1-dione

https://huagongshe.com/reaction/1023307

Reaction equation

Participants

RoleNameHCIDCharge
Reactant1,4-DibromobenzeneHCID 7804—
ReactantBinap, (A+-)-HCID 634876—
ReactantThiomorpholine 1,1-dioxideHCID 6484228—
ReactantSodium t-butoxideHCID 23676156—
CatalystBis(dibenzylideneacetone)palladiumHCID 9811564—
SolventTolueneHCID 1140—
Product4-(4-Bromophenyl)-1lambda~6~,4-thiazinane-1,1-dioneHCID 44629765—

Reaction Conditions

Temperature80 °C

Reaction Steps

A mixture of 1,4-dibromobenzene (118 mg, 0.5 mmol), thiomorpholine-1,1-dioxide (68 mg, 0.5 mmol), Pd2 dba3 (12 mg, 2.5 mol %), BINAP (24 mg, 7.5 mol %), sodium 2-methylpropan-2-olate (72 mg, 0.75 mmol) and toluene (2 mL) was stirred at 80° C. for overnight. The reaction mixture was cooled down to room temperature and worked-up. The residue was purified on slilica gel flash column chromatography (eluent: 0-50% EtOAc in hexane) to afford 4-(4-bromophenyl)thiomorpholine-1,1-dioxide as a white solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08722692B2
Source datasetuspto-grants-2014_05
ORD IDord-2c52fa3306c447fc92ae716e9465720e
Source noteuspto-grants-2014_05