Methyl iodide → 4-Bromo-2-butyl-6-fluoro-5-methoxy-1-indanone

A mixture of 4-bromo-2-butyl-6-fluoro-5-hydroxy-1-indanone (2.17 g, 7.23 mmol), N,N-dimethylformamide (14.5 mL), methyl iodide (0.675 mL, 10.84 mmol), and sodium bicarbonate (1.50 g, 18.1 mmol) was stirred at room temperature for 17 hours. The solvent was evaporated under vacuum. The residue in EtOAc (150 mL) was washed with water (5×100 mL) and brine (50 mL), dried over MgSO4, filtered, and evaporated under vacuum to an oil (2.29 g). The crude product was dissolved in CH2CL2 (5 mL) and the solution filtered through a pad of EM silica gel 60 (20 mL) using an additional 60 mL of CH2Cl2 to elute the silica gel. The CH2Cl2 filtrate was evaporated under vacuum to afford 4-bromo-2-butyl-6-fluoro-5-methoxy-1-indanone (1.86 g) as a pink oil.

1. customThe solvent was evaporated under vacuum
2. washThe residue in EtOAc (150 mL) was washed with water (5×100 mL) and brine (50 mL)
3. dry with materialdried over MgSO4
4. filtrationfiltered
5. customevaporated under vacuum to an oil (2.29 g)
6. dissolutionThe crude product was dissolved in CH2CL2 (5 mL)
7. filtrationthe solution filtered through a pad of EM silica gel 60 (20 mL)
8. washto elute the silica gel
9. customThe CH2Cl2 filtrate was evaporated under vacuum

ORDレコード

ord-835f01ea929a484fbdde0611e5ce74b3

出典データセット

uspto-grants-2006_08

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07087599B2