반응 #68554

반응 방정식

MeMgBr

4-bromo-2-chloro-N-methoxy-N-methylbenzamide

methylmagnesium bromide

diethyl ether

→

1-(4-bromo-2-chlorophenyl)ethanone

용매

THF

반응 조건

후처리

1. 1
   기타at −5° C.
2. 2
   workup.WAITAfter an additional hour
3. 3
   기타Reaction
4. 4
   기타quenched with sat NH4Cl (10 mL)
5. 5
   기타resulting white cake
6. 6
   세척washed repeatedly with diethyl ether
7. 7
   세척Combined organics washed with water

실험 절차

To a stirring solution of 4-bromo-2-chloro-N-methoxy-N-methylbenzamide (890 mg, 3195 μmol) in THF (10 mL) at −5° C. under nitrogen was slowly added methylmagnesium bromide 3.0 m in diethyl ether (1278 μl, 3834 μmol). After 30 min another 1.3 mL (3.8 mmol; 1.2 eq) of MeMgBr added at 23° C. After an additional hour, LCMS suggests 95% conversion. Reaction quenched with sat NH4Cl (10 mL) and resulting white cake washed repeatedly with diethyl ether. Combined organics washed with water and sat NaCl then pushed through a plug of silica (10 g). 1-(4-bromo-2-chlorophenyl)ethanone isolated as a colorless oil.

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