Reaction #155409

Reaction equation

potassium carbonate

Benzyl bromide

4-formylbenzeneboronic acid

citric acid

→

title compound

Yield 83.0%

4-Benzylbenzaldehyde

Yield 83.0%

Solvents

tetrahydrofuran

Conditions

Workup

1. 1
   Temperatureto cool to ambient temperature
2. 2
   Extractionextracted with ethyl acetate (3-fold 50 mL)
3. 3
   WashThe combined organic extracts were washed with brine (100 mL)
4. 4
   Dryingdried (magnesium sulphate)
5. 5
   Otherthe solvent removed in vacuo
6. 6
   OtherThe resulting oil was purified by column chromatography on silica gel eluting with ethyl acetate

Procedure

Benzyl bromide (41 g, 240 mmol), 4-formylbenzeneboronic acid (28 g, 186.7 mmol), palladium tetrakis triphenyl phosphine (7.9 g, 6.84 mmol) and potassium carbonate (84.7 g, 613 mmol) were combined in tetrahydrofuran (620 mL) and heated at 80° C. under nitrogen for 8 hours. The resulting suspension was allowed to cool to ambient temperature and stirred overnight. The reaction mixture was poured into 10% citric acid (50 mL) and extracted with ethyl acetate (3-fold 50 mL). The combined organic extracts were washed with brine (100 mL) and dried (magnesium sulphate) and the solvent removed in vacuo. The resulting oil was purified by column chromatography on silica gel eluting with ethyl acetate:heptane, (0:1 changing to 1:5, by volume) to give the title compound as a colourless oil, 83% yield, 30.45 g.

Source