تفاعل #2075726

معادلة التفاعل

DMF

1-Bromo-4-chloro-2-fluoro-3-methoxybenzene

n-Butyllithium

→

title compound

المردود 61.0%

4-Chloro-2-fluoro-3-methoxybenzaldehyde

المردود 61.0%

المذيبات

diethyl ether

ظروف التفاعل

المعالجة

1. 1
   أخرى7,300,907 for preparation)
2. 2
   أخرىthe temperature below −70° C.
3. 3
   workup.ADDITIONduring the addition
4. 4
   أخرىthe temperature below −60° C
5. 5
   درجة الحرارةto warm to ambient temperature
6. 6
   أخرىquenched with water
7. 7
   أخرىThe organic phase was dried
8. 8
   تركيزconcentrated
9. 9
   أخرىThe product was purified by flash chromatography on silica gel (hexane/ethyl acetate gradient)

الإجراء التجريبي

1-Bromo-4-chloro-2-fluoro-3-methoxybenzene (23.7 g, 99 mmol, see U.S. Pat. No. 7,300,907 for preparation) was dissolved in dry diethyl ether and cooled to −78° C. 2.5M n-Butyllithium in hexanes (44 mL, 110 mmol) was added in portions, keeping the temperature below −70° C. during the addition. DMF (15.5 mL, 200 mmol) was then added in portions, keeping the temperature below −60° C. The reaction mixture was then allowed to warm to ambient temperature and quenched with water. The organic phase was dried and concentrated. The product was purified by flash chromatography on silica gel (hexane/ethyl acetate gradient) to yield the title compound in sufficient purity for subsequent reactions (11.4 g, 61% yield): 1H NMR (CDCl3) δ 10.32 (s, 1H), 7.55 (m, 1H), 7.3 (m, 1H), 4.05 (d, 3H).

المصدر