تفاعل #646237

معادلة التفاعل

DMF

i-PrMgCl

103

3-chloro-5-(3,6-dibromo-2-fluoro-phenoxy)-benzonitrile

→

3-(6-bromo-2-fluoro-3-formyl-phenoxy)-5-chloro-benzonitrile

المردود 98.0%

المذيبات

toluene

THF

toluene

ظروف التفاعل

المعالجة

1. 1
   أخرىthen transferred by cannula to a flask
2. 2
   أخرىThe solution was quenched with aqueous NH4Cl
3. 3
   workup.ADDITIONdiluted with EtOAc
4. 4
   أخرىThe organic layer was separated
5. 5
   غسيلwashed with brine
6. 6
   أخرىdried
7. 7
   أخرىevaporated
8. 8
   أخرىThe crude product was purified by SiO2 by chromatography
9. 9
   غسيلeluting with 20% EtOAc/hexanes

الإجراء التجريبي

A solution of i-PrMgCl (17.3 mL of a 2 M solution in THF, 1.75 equiv) was added slowly to a solution of the 103 (8.0 g, 19.7 mmol) in toluene (160 mL) at −78 C. The solution was aged for 1.5 h then transferred by cannula to a flask containing DMF (2.3 mL, 1.5 equiv) in toluene (30 mL). The solution was quenched with aqueous NH4Cl, and diluted with EtOAc. The organic layer was separated, washed with brine, dried, and evaporated. The crude product was purified by SiO2 by chromatography eluting with 20% EtOAc/hexanes to afford 6.5 g (98%) of 3-(6-bromo-2-fluoro-3-formyl-phenoxy)-5-chloro-benzonitrile (105) as a yellow solid.

المصدر