반응 #79339

반응 방정식

2-Bromo-5-fluoro-N-methoxy-N-methylbenzamide

Methyl magnesium bromide

→

1-(2-bromo-5-fluorophenyl)ethanone

수율 93.0%

용매

THF

반응 조건

후처리

1. 1
   온도The solution was warmed to room temperature
2. 2
   온도The solution was cooled to 0° C.
3. 3
   기타quenched with HCl/EtOH (9 mL, 4 M solution)
4. 4
   기타The reaction mixture was transferred to a separatory funnel
5. 5
   workup.ADDITIONdiluted with H2O (30 mL)
6. 6
   추출extracted with Ethyl Acetate (2×40 mL)
7. 7
   세척The combined organic extracts were washed with H2O, brine
8. 8
   건조dried over Na2SO4
9. 9
   농축The solution was concentrated

실험 절차

2-Bromo-5-fluoro-N-methoxy-N-methylbenzamide (4.0 g, 0.015 mol) was dissolved in THF (30 mL) and the solution was cooled to 0° C. under N2blanket. Methyl magnesium bromide (15.26 mL, 0.046 mol) was added dropwise over 30 min. The solution was warmed to room temperature and stirred for 1 hour. The solution was cooled to 0° C. and quenched with HCl/EtOH (9 mL, 4 M solution). The reaction mixture was transferred to a separatory funnel, diluted with H2O (30 mL), and extracted with Ethyl Acetate (2×40 mL). The combined organic extracts were washed with H2O, brine, and dried over Na2SO4. The solution was concentrated to afford 1-(2-bromo-5-fluorophenyl)ethanone as a yellow oil in 93% yield . This material was used in the subsequent step without further purification. 1H NMR (CDCl3, 500 MHz) δ2.61 (s, 3H), 7.00-7.04 (m, 1H) 7.15-7.18 (m, 1H), 7.53-7.59 (m, 1H).

출처