Reaction #216978

Reaction equation

benzylmagnesium chloride

1-bromo-4-iodobenzene

→

title compound

Yield 80.8%

1-Bromo-4-(phenylmethyl)benzene

Yield 80.8%

Solvents

—

0

THF

THF

Conditions

Workup

1. 1
   workup.STIRRINGThe reaction was stirred at room temperature for 16 hours
2. 2
   Otherquenched with 50 mL of 2M hydro-chloric acid
3. 3
   ExtractionThe mixture was extracted thrice with hexanes
4. 4
   Washwashed once with saturated sodium bicarbonate solution and once with 10% sodium thiosulfate
5. 5
   ExtractionThe organic extract
6. 6
   Dryingwas dried (MgSO4)
7. 7
   Otherevaporated
8. 8
   OtherThe crude product was purified by flash chromatography on silica gel (5×25 cm column, hexanes as elutent)

Procedure

To a stirred solution of 21 mL (42 mmol, 2.0M in THF) of benzylmagnesium chloride at room temperature under nitrogen was added a solution of 6.80 g (50.0 mmol) of thrice-fused zinc chloride in 0 50 mL of THF. The resulting tan slurry was stirred for 1 hour. To this slurry was added 10.0 g (35.3 mmol) 1-bromo-4-iodobenzene and 450 mg (0.4 mmol) of tetrakis(tri-phenylphosphine)palladium in 30 mL of THF. The reaction was stirred at room temperature for 16 hours and then quenched with 50 mL of 2M hydro-chloric acid. The mixture was extracted thrice with hexanes, the extracts combined, washed once with saturated sodium bicarbonate solution and once with 10% sodium thiosulfate. The organic extract was dried (MgSO4) and evaporated. The crude product was purified by flash chromatography on silica gel (5×25 cm column, hexanes as elutent) to give 7.05 g (80%) of title compound as a colorless oil.

Source