반응 #47954

반응 방정식

2-amino-5-fluoro-N-methoxy-N-methylbenzamide

phenylmagnesium bromide

phenylmagnesium bromide

→

(2-amino-5-fluorophenyl)(phenyl)methanone

용매

THF

THF

THF

CH2Cl2

반응 조건

후처리

1. 1
   workup.STIRRINGthe reaction stirred at −78° C. for another hour
2. 2
   기타quenched with saturated ammonium chloride solution (300 mL)
3. 3
   기타The layers were separated
4. 4
   세척the organic one washed with brine (300 mL)
5. 5
   건조dried over Na2SO4
6. 6
   여과filtered
7. 7
   농축concentrated in vacuo
8. 8
   기타Purification by normal phase chromatography (3-8% MeOH/CH2Cl2)

실험 절차

To a −78° C. solution of 2-amino-5-fluoro-N-methoxy-N-methylbenzamide in THF (100 mL) was added 1M phenylmagnesium bromide in THF (124.12 mL, 124.12 mmol). The reaction was stirred from −78° C. to ambient temperature over 3.5 h and then cooled again to −78° C. Additional 1M phenylmagnesium bromide in THF (62.06 mL, 62.06 mmol) was added and the reaction stirred at −78° C. for another hour. The reaction was then diluted with CH2Cl2 (500 mL) and quenched with saturated ammonium chloride solution (300 mL). The layers were separated and the organic one washed with brine (300 mL), dried over Na2SO4, filtered and concentrated in vacuo. Purification by normal phase chromatography (3-8% MeOH/CH2Cl2) yielded (2-amino-5-fluorophenyl)(phenyl)methanone as a yellow solid. 1H NMR (CDCl3, 400 MHz) 7.63 (m, 2H, ArH); 7.55 (m, 1H, ArH); 7.47 (m, 2H, ArH); 7.15 (m, 1H, ArH); 7.08 (m, 1H, ArH); 6.70 (m, 1H, ArH); 5.91 (s, NH2); MS (Electrospray): m/z 216.1 (M+H).

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