تفاعل #2336548

معادلة التفاعل

1-bromo-4-chloro-2-fluorobenzene

LDA

DMF

→

3-bromo-6-chloro-2-fluorobenzaldehyde

المردود 169.0%

المذيبات

THF

THF

THF

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONAfter addition the solution
2. 2
   درجة الحرارةcooled to −50° C.
3. 3
   درجة الحرارةthe reaction mixture was warmed to ambient temperature
4. 4
   أخرىThe reaction was quenched with water (250 mL)
5. 5
   استخلاصextracted with ethyl acetate (2×150 mL)
6. 6
   تجفيفthe combined organic phases were dried (sodium sulfate)
7. 7
   تركيزconcentrated
8. 8
   أخرىThe solid residue was recrystallized from hexane

الإجراء التجريبي

A solution of 1-bromo-4-chloro-2-fluorobenzene (20.4 g, 0.100 mol) in THF (50 mL) was slowly added to LDA (0.125 mol) in THF (600 mL) at −50° C. After addition the solution was warmed to −20° C. and then cooled to −50° C. and a solution of DMF (14.6 g, 0.20 mol) in THF (50 mL) was slowly added and the reaction mixture was warmed to ambient temperature. The reaction was quenched with water (250 mL) and extracted with ethyl acetate (2×150 mL) and the combined organic phases were dried (sodium sulfate) and concentrated. The solid residue was recrystallized from hexane to give 3-bromo-6-chloro-2-fluorobenzaldehyde (40.0 g, 0.169 mol): mp 92-93° C.

المصدر