Bromine → 5-Bromo-2-ethylbenzaldehyde

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-ethyl-benzaldehyde (5.00 g, 37.3 mmol) in CH2Cl2 (23 mL) was carefully added AlCl3 (8.70 g, 65.2 mmol). The mixture was cooled to 0° C. and a solution of bromine (1.9 mL, 37.2 mmol) in CH2Cl2 (23 mL) was added over 6 hours. The reaction mixture was stirred at room temperature overnight. The mixture was poured onto an ice/water mixture and stirred for 10 minutes. The aqueous layer was extracted with EtOAc (2×). The combined organic layers were washed with 2 M HCl, saturated aqueous NaHCO3 and brine, dried over MgSO4, filtered and concentrated. The residue was purified by chromatography on silica gel (heptane/EtOAc) to afford INT 35.

Provenance & Evidence