Reaktion #489990

Reaktionsgleichung

aluminum chloride

4-bromo-2-chloro-1-[(3-methylbut-3-en-1-yl)sulfanyl]benzene

NaOH

→

desired product

6-bromo-8-chloro-4,4-dimethyl-3,4-dihydro-2H-thiochromene

Lösungsmittel

dichloromethane

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeto give a light yellow solution
2. 2
   Temperaturto warm to room temperature
3. 3
   workup.ADDITIONpoured into an Erlenmeyer flask
4. 4
   ExtraktionThe mixture was extracted with dichloromethane (2×, 40.0 mL)
5. 5
   Trocknenthe combined organic layers were dried over Na2SO4
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated under vacuum
8. 8
   SonstigeThe crude residue was purified by silica gel chromatography
9. 9
   Wascheneluting with 0-20% EtOAc/hexanes

Vorschrift

To a mixture of aluminum chloride (0.58 g, 4.34 mmol) and dichloromethane (23.2 mL) cooled to −78° C. was added 4-bromo-2-chloro-1-[(3-methylbut-3-en-1-yl)sulfanyl]benzene (1.15 g, 3.94 mmol) in dichloromethane (6.00 mL) via a cannula to give a light yellow solution. The reaction mixture was allowed to warm to room temperature, stirred for 5 minutes, and then poured into an Erlenmeyer flask containing a cold 10% aqueous NaOH solution (75.0 mL). The mixture was extracted with dichloromethane (2×, 40.0 mL) and the combined organic layers were dried over Na2SO4, filtered and concentrated under vacuum. The crude residue was purified by silica gel chromatography eluting with 0-20% EtOAc/hexanes to afford the desired product as a pale-yellow oil.

Quelle