Diisobutylaluminum hydride → HCID 57527160, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl 2-bromobenzo[d]thiazole-6-carboxylate (5.0 g, 17.5 mmol) from Step 1 of this Example in anhydrous CH2Cl2 was added DIBAL-H (1.0 M in CH2Cl2, 36.7 mL, 36.7 mmol) slowly at −78° C. The solution was stirred at −78° C. for 2 h. The resulting mixture was quenched with 10 mL of saturated aq sodium potassium tartrate at −78° C. After slowly warming to 0° C., the mixture was further treated with 50 mL of saturated aq sodium potassium tartrate and stirred at rt for 2 h. The aqueous layer was separated and extracted with CH2Cl2 (3×100 mL). The combined organic layers were washed with brine, dried over MgSO4, and concentrated under reduced pressure. The crude product was purified on a silica gel column using a mixture of EtOAc-hexanes (2:3, v/v) as eluent to give (2-bromobenzo[d]thiazol-6-yl)methanol as a white solid (3.4 g, 80%). 1H NMR (300 MHz, CDCl3) δ 7.96 (d, J=8.3 Hz, 1H), 7.85 (s, 1H), 7.45 (dd, J=1.4, 8.4 Hz, 1H), 4.83 (s, 2H), 1.86 (br s, 1H). LCMS (ESI) m/z 244, 246 (M+H)+.

Provenance & Evidence