Sodium borohydride → (2,6-Dibromo-4-fluorophenyl)methanol

Temperature

10 °C

To a solution of 101h (20 g, 71 mmol) in EtOH (500 mL) was added NaBH4 (10 g, 284 mmol). The mixture was stirred at room temperature (10° C.) for 4 h and TLC showed the start material disappeared. The reaction was quenched by aqueous HCl solution (150 mL, 1M) and evaporated in vacuo until most of EtOH was distilled. The residue was extracted by ethyl acetate (500 mL×3). The organic layers were combined, dried with Na2SO4, and evaporated in vacuo. The residue was purified by silica-gel column chromatography eluting with petroleum ether/ethyl acetate (from 50:1 to 20:1) to give 101i as a white solid (15 g, 75%). MS: [M−OH]+ 267. 1H NMR (500 MHz, DMSO-d6) δ 7.68 (d, J=8.5, 2H), 5.23 (s, 1H), 4.71 (s, 2H).

1. customThe reaction was quenched by aqueous HCl solution (150 mL, 1M)
2. customevaporated in vacuo until most of EtOH
3. distillationwas distilled
4. extractionThe residue was extracted by ethyl acetate (500 mL×3)
5. dry with materialdried with Na2SO4
6. customevaporated in vacuo
7. customThe residue was purified by silica-gel column chromatography
8. washeluting with petroleum ether/ethyl acetate (from 50:1 to 20:1)

ORD record

ord-a590051e63164eb3a037c32cb042dff6

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08722676B2