Chloride → HCID 86700143, compound

Participants

Reaction Steps

To a mixture of 2-bromo-5-methylbenzo[d]thiazol-7-ol (2.48 g, 10.16 mmol) in dichloromethane (100 mL) at 0° C. was added triethylamine (1.42 mL, 10.16 mmol) to give a clear solution. Titaniuim(IV) chloride (1.0M in CH2Cl2, 10.67 mL, 10.67 mmol) was added slowly to give an orange reaction mixture that was stirred for 30 minutes. A solution of cracked ethyl glyoxalate (1.04 g, 10.16 mmol) in CH2Cl2 (1 mL) was added over 2 minutes and reaction mixture was stirred at room temperature for 2.5 h. Reaction mixture was quenched with Rochelle's salt and stirred at room temperature for 2 h, diluted with CH2Cl2, and aqueous layer extracted with CH2Cl2 (2×). The combined organic layer was dried (MgSO4), filtered and concentrated. Purification by CombiFlash (40 g, 0 to 30% EtOAc/Hex) gave product contaminated with ethyl 2-(2-bromo-7-hydroxy-5-methylbenzo[d]thiazol-6-yl)-2-hydroxyacetate. LCMS-ESI+: calc'd for C12H13ClNO3S: 302.8 (M+H+); Found: 302.1 (M+H+).

Provenance & Evidence