2-Fluorophenol → 1-(2,2-Diethoxyethoxy)-2-fluorobenzene

Temperature

110 °C

A stirred mixture of 2-fluorophenol (1.00 g, 8.92 mmol), 2-bromo-1,1-diethoxyethane (1.75 g, 8.92 mmol), and K2CO3 (1.47 g, 10.7 mmol) in anhydrous DMF (10 mL) was heated at 110° C. overnight. The reaction mixture was poured into ice cold water (15 mL) and extracted with EtOAc (2×100 mL). The EtOAc solution was washed with water (25 mL) and brine (25 mL), dried over anhydrous Na2SO4, filtered, and evaporated to dryness under reduced pressure. The residue was purified by MPLC on silica gel using a mixture of EtOAc and hexane as eluent to give 1-(2,2-diethoxyethoxy)-2-fluorobenzene (1.65 g, 81%) as a viscous liquid. 1H NMR (400 MHz, CDCl3): δ 7.09-6.96 (m, 3H), 6.93-6.87 (m, 1H), 4.85 (t, 1H, J=5.2 Hz), 4.07 (d, 2H, J=5.2 Hz), 3.82-3.74 (m, 2H), 3.69-3.61 (m, 2H), 1.24 (t, 6H, J=7.0 Hz).

1. extractionextracted with EtOAc (2×100 mL)
2. washThe EtOAc solution was washed with water (25 mL) and brine (25 mL)
3. dry with materialdried over anhydrous Na2SO4
4. filtrationfiltered
5. customevaporated to dryness under reduced pressure
6. customThe residue was purified by MPLC on silica gel using
7. additiona mixture of EtOAc and hexane as eluent

ORD record

ord-a678069a189541a1941fb2a17d9057b7

Source dataset

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08080568B1