Reaktion #43282

Reaktionsgleichung

CuCN

allyl bromide

ethyl 3-iodobenzoate

i-PrMgCl

→

compound 7

Ausbeute 68.4%

3-Allyl-benzoic acid ethyl ester

Ausbeute 68.4%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas quenched by addition of 50 mL saturated NH4Cl solution
2. 2
   workup.ADDITIONWater (30 mL) was added
3. 3
   Extraktionthe resulting mixture was extracted with ethyl acetate (3×50 mL)
4. 4
   TrocknenThe combined ethyl acetate solution was dried (MgSO4)
5. 5
   Filtrationfiltered
6. 6
   Sonstigeevaporated
7. 7
   SonstigePurification by flash chromatography on silica gel (5% ethyl acetate/hexanes→10%)

Vorschrift

A −45° C. solution of ethyl 3-iodobenzoate (2.434 g, 8.8 mmol) in 40 mL THF was treated with i-PrMgCl (4.8 mL, 9.6 mmol, 2 M/ether). After 1 h, allyl bromide (1.6 mL, 18.9 mmol) was added followed by CuCN (79 mg, 0.88 mmol). The reaction was stirred for 1 h and then was quenched by addition of 50 mL saturated NH4Cl solution. Water (30 mL) was added and the resulting mixture was extracted with ethyl acetate (3×50 mL). The combined ethyl acetate solution was dried (MgSO4), filtered and evaporated. Purification by flash chromatography on silica gel (5% ethyl acetate/hexanes→10%) gave compound 7 (1.145 g, 68%).

Quelle