Diethyl Ether → Octane, 1-bromo-8-fluoro-

Temperature

-78 °C

A solution of 8-bromooctan-1-ol (Hendry et al., J. Chem. Ecol., 1, 317, 1975), (2.50 g, 11.9 mmol) in methylene chloride (about 3 ml) is slowly added to a stirred solution of diethylaminosulfur trifluoride (DAST) (Middleton, J. Org. Chem, 40, 574, 1975) (1.5 mL, 11.9 mmol) in methylene chloride (10 mL), cooled to -78° C. After the addition is completed, the reaction mixture is warmed to 25° C. and saturated aqueous sodium bicarbonate (about 5 mL) is added, followed by dilution with ether (about 200 mL). The organic layer is then separated, and washed with water (20 mL), saturated sodium bicarbonate (20 mL) and then dried (MgSO4). The volatiles are removed in vacuo and the crude product is purified by flash chromatography using hexane/ethyl acetate, (95.5, v/v) to afford 8-bromo-fluoro-octane (1.54 g, 61%) as a clear colorless liquid: Rf=0.70, hexane/ethyl acetate (7:3, v/v); IR (film) ν2850-3000 (alkane CH) and 1H-NMR (CDCl3) δ1.15-2.0 (m, 12H), 3.39 (t, J=6 Hz, 2H), 4.42 (dt, J=48 Hz, 6 Hz, 2H).

1. additionAfter the addition
2. temperaturethe reaction mixture is warmed to 25° C.
3. customThe organic layer is then separated
4. washwashed with water (20 mL), saturated sodium bicarbonate (20 mL)
5. dry with materialdried (MgSO4)
6. customThe volatiles are removed in vacuo
7. customthe crude product is purified by flash chromatography

ORD record

ord-75032fc405b949d29e2ca1f049d83155

Source dataset

uspto-grants-1984_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04455441