Hydrochloric Acid → 1-(2-Bromothiazol-5-yl)ethanol

Participants

Reaction Conditions

Reaction Steps

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of commercially available 2-bromo-thiazole-5-carbaldehyde (1.96 g, 10.00 mmol) in CH2Cl2 (20 mL) was treated at 0° C. with trimethylaluminum (15 mL of a 2M solution in toluene, 30.00 mmol). The reaction mixture was then stirred at 0° C. for 45 min. CH2Cl2 (100 mL) was then added followed by sat. aq. NH4Cl (100 mL). The mixture was then treated with 1N HCl (50 mL) and the aq. layer was extracted with CH2Cl2 (150 mL). The combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure to give the title compound as an orange oil. TLC:rf (1:1 hept-EA)=0.38. LC-MS-conditions 02: tR=0.70 min; [M+H]+=208.38.

Provenance & Evidence