Pentane → HCID 68650155, compound

Temperature

-78 °C

A solution of 2-bromo-4-fluoro-1-methoxybenzene (2.0 g, 9.75 mmol) in 20 mL of anhydrous THF was cooled to −78° C. Then 1.7M solution of t-BuLi in pentane (13.0 mL, 22.1 mmol) was added dropwise. The mixture was stirred at −78° C. for 10 min, then R-(+)-propylene oxide (670 mg, 11.55 mmol) was added and the mixture was allowed to warm to 0° C. overnight. The mixture was quenched with 2 mL of sat. NH4Cl and then conc. HCl was added dropwise to pH 8. The mixture was extracted with EtOAc (2×20 mL), the extract was dried over Na2SO4 and evaporated to give crude oil, which was purified by column (silica gel, EtOAc/hexane 1:9) to give (2R)-1-(5-fluoro-2-methoxyphenyl)propan-2-ol (531 mg, 30%). 1H NMR (300 MHz, CDCl3): δ 6.88 (m, 2H), 6.78 (m, 1H), 4.06 (m, 1H), 3.81 (s, 3H), 2.66-2.84 (m, 2H), 1.92 (d, J=3.96 Hz, 1H), 1.22 (d, J=6.21 Hz, 3H).

1. temperatureto warm to 0° C. overnight
2. customThe mixture was quenched with 2 mL of sat. NH4Cl
3. additionconc. HCl was added dropwise to pH 8
4. extractionThe mixture was extracted with EtOAc (2×20 mL)
5. dry with materialthe extract was dried over Na2SO4
6. customevaporated
7. customto give crude oil, which
8. customwas purified by column (silica gel, EtOAc/hexane 1:9)

ORD record

ord-5fafa5aa76584366bd15780356509a3c

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08815906B2