Reaction #12063

Reaction equation

4-fluorophenylmethyl chloride

magnesium

2-bromo-indene

chloride

→

2-(4-fluorophenylmethyl)indene

Solvents

ether

ether

ether

Conditions

Workup

1. 1
   TemperatureThe system was carefully heated
2. 2
   Otherafter initiation of the reaction
3. 3
   Temperaturewhile maintain a gentle reflux
4. 4
   TemperatureAfter refluxing for 1.5 hours
5. 5
   Temperaturethe Grignard solution was cooled
6. 6
   TemperatureThe system was gently heated
7. 7
   Temperatureto reflux overnight
8. 8
   Temperaturecooled
9. 9
   Otherquenched
10. 10
    workup.ADDITIONby adding 150 mL of 1.0 M aqueous hydrochloric acid
11. 11
    OtherThe product was isolated
12. 12
    Otherpurified (hexanes/silica) as for 2-benzyl-indene

Procedure

To a suspension of freshly ground magnesium (0.58 g, 23 mmol) in 100 mL of ether was added about 3 mL of a 15 mL ether solution containing 3.0 g (21 mmol) of 4-fluorophenylmethyl chloride. The system was carefully heated and after initiation of the reaction, the remaining chloride solution added over 30 minutes while maintain a gentle reflux. After refluxing for 1.5 hours, the Grignard solution was cooled and cannulated to a mixture of 3.65 g (19 mmol) of 2-bromo-indene, 150 mg (0.20 mmol) of NiCl2(dppp) and 100 mL of ether. The system was gently heated to reflux overnight and then cooled and quenched by adding 150 mL of 1.0 M aqueous hydrochloric acid. The product was isolated and purified (hexanes/silica) as for 2-benzyl-indene. Yield: 3.45 g, 74 percent

Source