Hydrochloric Acid → HCID 67460080, compound

Temperature

-5 °C

Sodium nitrite (0.172 g, 2.5 mmol) was added to a stirred solution of 2-chloro-6-fluoro-3-methyl-phenylamine (0.400 g, 2.5 mmol) in water (20 ml) and 37% aqueous hydrogen chloride (5 ml) at −5° C. The mixture was stirred at −5° C. for 5 minutes and then added in one pot to a solution of copper (I) chloride (0.742 g, 7.5 mmol) in 37% aqueous hydrogen chloride (5 ml) whilst maintaining the temperature at −5 to 0° C. The reaction mixture was heated to 38° C. and stirred for 1 hr then the mixture was cooled and diethyl ether (20 ml) was added. The organic phase was separated and washed with 1N aqueous hydrogen chloride and then with water. The organic layer was then dried over sodium sulphate and concentrated in vacuo. The crude residue was purified by flash silica column chromatography, eluting with petroleum ether, to give 2,3-dichloro-1-fluoro-4-methylbenzene (0.090 g, 0.5 mmol) as a white solid.

1. temperaturewhilst maintaining the temperature at −5 to 0° C
2. temperatureThe reaction mixture was heated to 38° C.
3. stirringstirred for 1 hr
4. temperaturethe mixture was cooled
5. customThe organic phase was separated
6. washwashed with 1N aqueous hydrogen chloride
7. dry with materialThe organic layer was then dried over sodium sulphate
8. concentrationconcentrated in vacuo
9. customThe crude residue was purified by flash silica column chromatography
10. washeluting with petroleum ether

ORD record

ord-2f85d0d583db450384ee42d77248597e

Source dataset

uspto-grants-2011_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08048907B2