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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2181786Generated: November 1, 2026

Dichloromethane → 4-{[(S)-6-methylphenanthridin-5(6H)-yl]sulfonyl}phenol

https://huagongshe.com/reaction/2181786

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDichloromethaneHCID 6344—
ReactantCyclohexeneHCID 8079—
ReactantBoron tribromideHCID 25134—
Reactant(S)-5-(4-Methoxy-benzenesulfonyl)-6-methyl-5,6-dihydrophenanthridineHCID 58597406—
Product4-{[(S)-6-methylphenanthridin-5(6H)-yl]sulfonyl}phenolHCID 10450594—

Reaction Steps

The title compound was prepared from (S)-5-[(4-methoxyphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridine (0.32 g, 1.02 mmol), cyclohexene (0.26 mL, 2.54 mmol), and 1.0 M boron tribromide in dichloromethane (6.1 mL, 6.1 mmol) according to the procedure and in the same manner as described in Example 1, step b. The crude product was purified by column chromatography on silica gel, eluting with dichloromethane, to yield 4-{[(S)-6-methylphenanthridin-5(6H)-yl]sulfonyl}phenol* (0.25 g, 0.72 mmol, 71%) as a white, solid, single enantiomer, m.p. 176-178° C.;

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06894061B2
Source datasetuspto-grants-2005_05
ORD IDord-2713142395264046830e65c97cfd145c
Source noteuspto-grants-2005_05