반응 #1842035

반응 방정식

4-bromo-1-fluoro-2-iodobenzene

isopropylmagnesium chloride

NH4Cl

2-(allyloxy)-N-methoxy-N-methylacetamide

→

2-allyloxy-1-(5-bromo-2-fluoro-phenyl)ethanone

용매

THF

water

THF

반응 조건

후처리

1. 1
   workup.ADDITIONis added over about 60 minutes
2. 2
   기타the layers are separated
3. 3
   세척The organic layer is washed with water (7.2 mL/g)
4. 4
   농축The organic layer is concentrated while additional heptanes (4 mL/g)
5. 5
   workup.ADDITIONis added
6. 6
   기타to remove water and THF

실험 절차

Scheme 1, steps C and D: To 4-bromo-1-fluoro-2-iodobenzene (0.95 equiv.) in THF (4.6 mL/g) at 0° C. is added isopropylmagnesium chloride (1.0 equiv, 20 weight percent in THF). After about 60 minutes at 0° C., a solution of 2-(allyloxy)-N-methoxy-N-methylacetamide (1.0 equiv.) (Volumes for this stage are in mL/g of this compound) in THF (2.2 mL/g) is added over about 60 minutes. The reaction mixture is quenched into a solution of NH4Cl (4.3 equiv.) in water (5.8 mL/g) at 0° C. Heptanes (7.2 mL/g) is added as the mixture is warmed to room temperature, and the layers are separated. The organic layer is washed with water (7.2 mL/g). The organic layer is concentrated while additional heptanes (4 mL/g) is added to remove water and THF. The intermediate, 2-allyloxy-1-(5-bromo-2-fluoro-phenyl)ethanone is obtained as a solution in heptanes (approximately 20-25 weight %).

출처