Hydrochloric Acid → HCID 11823172, compound

Participants

Reaction Conditions

Reaction Steps

16.36 ml (26.18 mmol) of BuLi (1.6N/hexane) are added dropwise, with stirring and over 30 min, to a solution of 5 g (21.89 mmol) of 1-bromo-3-trimethylsilylbenzene prepared according to the protocol described in stage 3.1, in 40 ml of anhydrous Et2O, cooled to 0° C. and maintained under a nitrogen atmosphere. The stirring is continued at 0° C. for a further 30 min, and then maintained at ambient temperature for 90 min. 2.69 ml (34.91 mmol) of DMF, diluted in 17 ml of anhydrous Et2O, are subsequently introduced into the reaction mixture. After stirring for 3 h at ambient temperature, the reaction mixture is hydrolysed at 0° C. by successive additions of 10 ml of a concentrated HCl solution and 100 ml of water. The product is extracted with 3×50 ml of CH2Cl2. The combined organic phases are washed with 100 ml of water, dried over Na2SO4, filtered and evaporated under reduced pressure. The reaction crude is purified by flash chromatography on a silica gel column, elution being carried out with a gradient of 10 to 20% of CH2Cl2 in heptane, to give 1.82 g of expected 3-trimethylsilyl-benzaldehyde in the form of a yellow oil.

Provenance & Evidence