Methyl iodide → HCID 14672062, compound

Temperature

-78 °C

t-Butyllithium (1.7 ml of a 1.8M solution of hexane; 3 equiv.) is added to THF (1 ml) and cooled to -78° C. under argon with stirring, and a solution of 2-bromo-6-trifluoromethylphenol in dry THF (1 ml; 1 mmol) is added dropwise via syringe. The reaction is stirred 30 minutes, and then iodomethane (340 mg; 2.4 equiv.) is added dropwise via syringe at -78° C. under argon, with stirring. The mixture is allowed to warm to 0° C. with stirring over 15 minutes, and stirring is continued for 45 minutes more. The reaction is then quenched with 1N HCl (3 ml) and extracted from 1N HCl (10 ml) with 3×10 ml portions of ether. The combined ether portions are washed with water (3×20 ml portions: pH tests neutral), and the solution is then dried (MgSO4), filtered, and concentrated in vacuo to give crude 2-methyl-6 -trifluoromethylphenol, which is chromatographed on silica gel with 5% ether in petroleum ether to give pure product.

1. stirringThe reaction is stirred 30 minutes
2. stirringwith stirring
3. temperatureto warm to 0° C.
4. stirringwith stirring over 15 minutes
5. stirringstirring
6. customThe reaction is then quenched with 1N HCl (3 ml)
7. extractionextracted from 1N HCl (10 ml) with 3×10 ml portions of ether
8. washThe combined ether portions are washed with water (3×20 ml portions: pH tests neutral)
9. dry with materialthe solution is then dried (MgSO4)
10. filtrationfiltered
11. concentrationconcentrated in vacuo

ORD record

ord-4af469bed67b45d48a42923fc77d0f81

Source dataset

uspto-grants-1989_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04847303