反应详情

温度

90 °C

5-(benzyloxy)-7-bromobenzo[d]thiazole (0.65 g, 2.0 mmol), Pd2(dba)3 (95 mg, 0.10 mmol), and 2-Di-tert-butylphosphino-2′,4′,6′-triisopropylbiphenyl (180 mg, 0.42 mmol) were taken up in 1,4-dioxane (7.2 mL) under Ar. Aqueous 2 M KOH (3 mL, 6 mmol) was added and the mixture was heated to 90° C. After 35 min, the mixture was cooled to r.t. and was diluted with EtOAc (20 mL), water (15 mL), and brine (15 mL). The aqueous phase was and acidified with 3 M aqueous HCl (3 mL, 9 mmol). The phases were separated, and the organic phase was dried over Na2SO4, filtered, and concentrated to afford a crude residue that was purified by silica gel chromatography (10-60% EtOAc in hexanes) to provide 5-(benzyloxy)benzo[d]thiazol-7-ol 4.03B. LCMS-ESI+ (m/z): [M+H]+ calcd for C14H12NO2S: 258.1; found 257.8.

1. temperaturethe mixture was cooled to r.t.
2. customThe phases were separated
3. dry with materialthe organic phase was dried over Na2SO4
4. filtrationfiltered
5. concentrationconcentrated
6. customto afford a crude residue that
7. customwas purified by silica gel chromatography (10-60% EtOAc in hexanes)