Sodium Bicarbonate → HCID 66653294, compound

Participants

Reaction Conditions

Reaction Steps

The required (2-chloro-5-ethylphenyl)methanol was prepared as follows: To a nitrogen purged solution of ethyl 5-bromo-2-chlorobenzoate (4.3 mL, 25.1 mmol) in THF (100 mL) was added lithium chloride (2.12 g, 50.1 mmol) and Pd(dppf)Cl2 (0.82 g, 1 mmol). Subsequently, the mixture was cooled to −78° C., and a solution of diethylzinc in heptane (37.6 mL; 1.00 mol/l; 37.6 mmol) was added dropwise. The reaction mixture was allowed to come to RT overnight. The resulting reaction mixture was cooled to −10° C. and diluted with Et2O (300 mL). Subsequently, a 1 M aqueous HCl solution (150 mL) was added carefully. The layers were separated, and the organic layer was dried (Na2SO4), filtered, and concentrated in vacuo. The residue was purified by column chromatography (SiO2, Et2O:hexanes 5:95) to afford ethyl 2-chloro-5-ethylbenzoate (4.61 g). To a nitrogen purged solution of ethyl 2-chloro-5-ethyl-benzoate (1 g, 4.70 mmol) in THF (25 mL), was added diisobutylaluminiumhydride (14.11 mL; 14.11 mmol) in toluene, at −5° C. The reaction mixture was allowed to come to RT and stirred overnight. The resulting reaction mixture was cooled to −10° C. and a 5% aqueous NaHCO3-solution (10 mL) was added. The layers were separated, and the organic layer was dried (Na2SO4), filtered, and concentrated in vacuo. The residue was purified by column chromatography (SiO2, Et2O:hexanes 1:3 followed by Et2O:hexanes 1:1) to afford (2-chloro-6-ethylphenyl)methanol (0.59 g) which was used as such.

Provenance & Evidence