Hydrochloric Acid → Benzothiazole, 6-bromo-2-methyl-

In a mixed solvent of THF (200 mL) and NMP (20 mL) were dissolved 6-bromo-2-chlorobenzothiazole 1 (15 g, 60.4 mmol) and Fe(acac)3 (1.07 g, 3.02 mmol). To the obtained mixture was added at 0° C. 3M methyl magnesium bromide ethereal solution (24.14 ml, 72.4 mmol). It was stirred at room temperature for 1.5 hours. To the reaction mixture was added at 0° C. 3M methyl magnesium bromide ethereal solution (10.1 ml, 30.2 mmol). It was stirred at room temperatures for 1 hour. To the reaction mixture 1N aqueous hydrochloric acid and ethyl acetate. After extraction, the organic layer was washed with brine and dried over magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified with column chromatography to give Compound 53 (10.6 g, 46.5 mmol).

1. additionTo the obtained mixture was added at 0° C
2. additionTo the reaction mixture was added at 0° C
3. stirringIt was stirred at room temperatures for 1 hour
4. extractionAfter extraction
5. washthe organic layer was washed with brine
6. dry with materialdried over magnesium sulfate
7. customThe solvent was evaporated under reduced pressure
8. customThe residue was purified with column chromatography

ORD record

ord-c03da56814074640aadb6be28f54ff25

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08957219B2