Sodium borohydride → HCID 68015202, compound

(5-bromo-2-chloro-phenyl)-(4-ethoxy-3-fluoro-phenyl)methanone 4c (12.7 g, 35.5 mmol) was dissolved in 100 mL of mixed solution (THF and MeOH, v:v=1:1), followed by addition of sodium borohydride (2.68 g, 70 mmol) in batch in an ice bath. The reaction mixture was warmed and stirred for 30 minutes at room temperature. Thereafter, the reaction mixture was concentrated under reduced pressure after 15 mL acetone were added. The residue was dissolved in 150 mL ethyl acetate and washed with saturated sodium chloride solution (50 mL×2). The organic extract was combined, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure to obtain the title compound (5-bromo-2-chloro-phenyl)-(4-ethoxy-3-fluoro-phenyl)methanol 4d (12.7 g, orange grease), which was used directly in the next step without purification.

1. temperatureThe reaction mixture was warmed
2. concentrationThereafter, the reaction mixture was concentrated under reduced pressure after 15 mL acetone
3. additionwere added
4. dissolutionThe residue was dissolved in 150 mL ethyl acetate
5. washwashed with saturated sodium chloride solution (50 mL×2)
6. extractionThe organic extract
7. dry with materialdried over anhydrous magnesium sulfate
8. filtrationfiltered
9. concentrationThe filtrate was concentrated under reduced pressure

ORD record

ord-a1a438dbf26c4ecba98460307e7ad08d

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08609622B2