Réaction #581863

Équation de réaction

mesitylmagnesium bromide

PtBu3

2-bromo-1H-indene

→

2-Mesityl-1H-indene

Solvants

brine

THF

Conditions de réaction

Traitement

1. 1
   AutreThe organic layer was separated
2. 2
   Extractionthe aqueous layer was extracted with 3×100 ml of ether
3. 3
   SéchageThe combined organic fractions were dried over K2CO3
4. 4
   Autreevaporated to dryness
5. 5
   AutreThe product was isolated by flash chromatography on Silica Gel 60 (40-63 um, d 30 mm, 1 300 mm, eluent: hexanes-dichloromethane, 20:1, vol.)

Mode opératoire

A mixture of 50.0 ml (20.0 mmol) of 0.4 M mesitylmagnesium bromide in THF, 230 mg (0.40 mmol) of Pd(dba)2, 162 mg (0.80 mmol) of PtBu3, and 3.90 g (20.0 mmol) of 2-bromo-1H-indene was stirred for 48 h at ambient temperature. Then, to the resulting mixture 200 ml of brine was added. The organic layer was separated, and the aqueous layer was extracted with 3×100 ml of ether. The combined organic fractions were dried over K2CO3 and then evaporated to dryness. The product was isolated by flash chromatography on Silica Gel 60 (40-63 um, d 30 mm, 1 300 mm, eluent: hexanes-dichloromethane, 20:1, vol.). Yield 3.19 g (68%) of white solid.

Source