HCID 58707319, compound → HCID 58707309, compound

Temperature

0 °C

To a stirred solution of 5-Fluoro-2-methoxy-3-methylbenzaldehyde (1.2 g, 7.13 mmol) in dry diethyl ether (20 mL) at 0° C. was added methylmagnesium bromide of 3.0 M in ether (6.0 mL, 17.83 mmol). The reaction mixture was brought to room temperature and was stirred for 30 min then refluxed for 3 h. It was then cooled to 0° C. and quenched by adding saturated aqueous NH4Cl. The two liquid layers were separated. The aqueous layer was extracted with ether. The combined organic layers were washed with water, dried, and concentrated to the crude compound which was purified by silica gel column (10-25% ethyl acetate in hexanes) to afford 1-(5-fluoro-2-methoxy-3-methylphenyl)ethanol (1.0 g, 76%): 1H NMR (400 MHz, CDCl3): δ 7.12 (dd, 1H), 6.83 (dd, 1H), 4.72 (m, 1H), 3.81 (s, 3H), 2.38 (s, 3H), 1.47 (d, 3H).

1. customwas brought to room temperature
2. temperaturethen refluxed for 3 h
3. customquenched
4. additionby adding saturated aqueous NH4Cl
5. customThe two liquid layers were separated
6. extractionThe aqueous layer was extracted with ether
7. washThe combined organic layers were washed with water
8. customdried
9. concentrationconcentrated to the crude compound which
10. customwas purified by silica gel column (10-25% ethyl acetate in hexanes)

ORD record

ord-52a29cfd20474900b2743b795044ae36

Source dataset

uspto-grants-2011_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07968538B2