تفاعل #48540

معادلة التفاعل

iso-propylmagnesium chloride

3,5-dibromofluorobenzene

3,5-dibromo-fluoro-benzene

THF

THF

THF

THF

→

28

المردود 100.5%

3-bromo-5-fluoro-benzaldehyde

المردود 100.5%

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةwhile maintaining the temperature at ca. 0 C
2. 2
   غسيلAfter rinsing with THF (3×20 mL) the mixture
3. 3
   workup.ALIQUOTThe reaction was sampled by HPLC
4. 4
   درجة الحرارةcooled to ca. 0° C
5. 5
   workup.ADDITIONDMF was added over 0.5 h
6. 6
   درجة الحرارةwhile maintaining the temperature at ca. 0° C
7. 7
   workup.WAITThe mixture was aged 1.5 h at ca. 0° C.
8. 8
   درجة الحرارةwarmed slowly to ca. 20° C. overnight
9. 9
   workup.ALIQUOTAfter sampling by HPLC
10. 10
    workup.ADDITIONthe mixture was diluted with heptane (200 mL)
11. 11
    workup.ADDITIONwith a mixture of con HCl (120 mL)
12. 12
    workup.ADDITIONdiluted to 360 mL with water
13. 13
    workup.ADDITIONCon HCl (50 mL) was added
14. 14
    أخرىThe organic phase was separated
15. 15
    غسيلwashed with water (400 mL)
16. 16
    أخرىevaporated to dryness

الإجراء التجريبي

step 1—To a solution of iso-propylmagnesium chloride in THF (500 mL of a 2M solution in THF, 1.0 mol) and THF (200 mL) was added a solution of 3,5-dibromofluorobenzene (25; 200 g, 0.79 mol) in THF (100 mL) while maintaining the temperature at ca. 0 C. After rinsing with THF (3×20 mL) the mixture was aged for 2 h at ca. 0° C. and then warmed to ca. 20° C. and aged for 0.5 h. The reaction was sampled by HPLC and then cooled to ca. 0° C. DMF was added over 0.5 h while maintaining the temperature at ca. 0° C. The mixture was aged 1.5 h at ca. 0° C. and then warmed slowly to ca. 20° C. overnight. After sampling by HPLC, the mixture was diluted with heptane (200 mL) and then with a mixture of con HCl (120 mL) diluted to 360 mL with water. Con HCl (50 mL) was added to adjust the pH to <7. The organic phase was separated, washed with water (400 mL) and evaporated to dryness to afford 160.8 g (100.5%) of 28 as a yellow oil which solidified on standing.

المصدر