반응 #79338

반응 방정식

Triphenylphospine

2-Bromo-5-fluorobenzoic acid

N,O-Dimethylhydroxylamine hydrochloride

triethylamine

→

2-bromo-5-fluoro-N-methoxy-N-methylbenzamide

수율 73.0%

용매

methylene chloride

반응 조건

후처리

1. 1
   농축The solution was concentrated to an oil
2. 2
   workup.ADDITIONHexanes (100 mL) and Ethyl Acetate (100 mL) were added to the oil
3. 3
   workup.STIRRINGstirred for 1 hour
4. 4
   여과then filtered
5. 5
   농축The filtrate was concentrated
6. 6
   기타the residue was purified by chromatography (Hexanes/Ethyl Acetate) on silica gel

실험 절차

2-Bromo-5-fluorobenzoic acid (4.60 g, 0.02 mol), N,O-Dimethylhydroxylamine hydrochloride (2.05 g, 0.02 mol), carbon tertabromide (6.9 g, 0.02 mol) was added to mixture of methylene chloride (100 mL) and triethylamine (2.9 mL, 0.02 mol). Triphenylphospine (5.53 g, 0.02 mol) was added to the solution over 1 hour and stirred for another 1 hour. The solution was concentrated to an oil. Hexanes (100 mL) and Ethyl Acetate (100 mL) were added to the oil and stirred for 1 hour then filtered. The filtrate was concentrated and the residue was purified by chromatography (Hexanes/Ethyl Acetate) on silica gel to afford 2-bromo-5-fluoro-N-methoxy-N-methylbenzamide as a foamy white solid in 73% yield. 1H NMR (CDCl3, 500 MHz) δ3.00-3.98 (m, 6 H), 6.97-7.08 (m, 2H), 7.51-7.54 (m, 1H).

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