Reaction #1265373

Reaction equation

water

ethyl 2-bromobenzoate

4-(N,N,-dimethylaminomethyl)styrene

triethylamine

→

product

Yield 63.5%

Ethyl 2-(E-2-(4-(N,N-dimethylaminomethyl)phenyl)ethen-1-yl)benzoate

Yield 63.5%

Solvents

dimethylformamide

Conditions

Workup

1. 1
   ConcentrationThe reaction mixture was then concentrated in vacuo
2. 2
   Otherthe resulting residue was partitioned between ethyl acetate and water
3. 3
   OtherThe organic phase was separated off
4. 4
   Washwashed with water
5. 5
   Otherdried
6. 6
   Concentrationconcentrated in vacuo
7. 7
   OtherThe residue was then recrystallized from petroleum ether

Procedure

18.8 g (82 mmol) of ethyl 2-bromobenzoate, 17.2 g (107 mmol) of 4-(N,N,-dimethylaminomethyl)styrene [sic], 20.7 g (205 mmol) of triethylamine, 0.36 g of palladium(II) acetate and 0.96 g of tri(o-tolyl)phosphine were mixed in 200 ml of dimethylformamide and, after addition of 1 ml of water, stirred at 140° C. for 3 h. The reaction mixture was then concentrated in vacuo, and the resulting residue was partitioned between ethyl acetate and water. The organic phase was separated off, washed with water, dried and concentrated in vacuo. The residue was then recrystallized from petroleum ether. 16.1 g (63%) of the product were obtained.

Source