Reaktion #85696

Reaktionsgleichung

4-bromo-2-fluorobenzaldehyde

(R)-2-methylpropane-2-sulfinamide

→

(R,E)-N-(4-bromo-2-fluorobenzylidene)-2-methylpropane-2-sulfinamide

Ausbeute 103.0%

Lösungsmittel

DCE

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeTo an oven dried round bottom flask
2. 2
   SonstigeReaction mixture
3. 3
   SonstigeReaction mixture
4. 4
   Filtrationwas filtered through a pad celite
5. 5
   Waschenwashing the solids with CH2Cl2
6. 6
   EinengenThe filtrate was concentrated

Vorschrift

To an oven dried round bottom flask with stir bar was added 4-bromo-2-fluorobenzaldehyde (5 g, 24.6 mmol), (R)-2-methylpropane-2-sulfinamide (3.28 g, 27.1 mmol) and DCE (49 mL). To this mixture was then added copper (II) sulfate (5.90 g, 36.9 mmol). Reaction mixture was heated in a preheated oil bath to 55° C. for 18 hours. Reaction mixture was filtered through a pad celite, washing the solids with CH2Cl2. The filtrate was concentrated to afford a viscous yellow oil of (R,E)-N-(4-bromo-2-fluorobenzylidene)-2-methylpropane-2-sulfinamide (7.73 g, 25.2 mmol, 103% yield). 1H NMR (400 MHz, CDCl3) δ 1.27 (s, 9H) 7.31-7.42 (m, 2H) 7.87 (t, J=7.87 Hz, 1H) 8.83 (s, 1H). LCMS m/z 307.9 (M+H)+, Rt 1.01 min.

Quelle