Reaction #43280

Reaction equation

ether

4-bromobenzaldehyde

THF

→

4

Yield 76.0%

1-(4-Bromo-phenyl)-hexan-1-ol

Yield 76.0%

Conditions

Workup

1. 1
   Otherthe reaction was quenched by addition of 200 mL saturated ammonium chloride solution
2. 2
   ExtractionThe resulting mixture was extracted with ethyl acetate (3×100 mL)
3. 3
   Dryingthe combined ethyl acetate solution was dried (Na2SO4)
4. 4
   Filtrationfiltered
5. 5
   Otherevaporated
6. 6
   OtherPurification of the residue by flash chromatography on silica gel

Procedure

n-PentylMgBr (29 mL, 58 mmol, 2 M/ether) was added to a 0° C. solution of 4-bromobenzaldehyde (9.953 g, 54 mmol) in THF (100 mL). After 1 h, the reaction was quenched by addition of 200 mL saturated ammonium chloride solution. The resulting mixture was extracted with ethyl acetate (3×100 mL) and the combined ethyl acetate solution was dried (Na2SO4), filtered and evaporated. Purification of the residue by flash chromatography on silica gel gave 4 (10.501 g, 76%).

Source