1,2-Dichloroethane → 4-bromo-2-(hydroxymethyl)-N-methylbenzamide

A 500 mL RB flask was charged with aluminum(III) chloride (4.1 g, 31 mmol) and 10 mL of 1,2-dichloroethane (90 ml, 1142 mmol), then cooled to 0° C. A separate 250 mL flask was charged with 90 mL of 1,2-dichloroethane (90 ml, 1142 mmol) and cooled to 0° C.; methylamine (gas) (1.8 g, 59 mmol) was bubbled through the solution for 10 minutes. The dichloroethane solution was slowly poured into the aluminum chloride solution, resulting in the formation of a thick white slush. This was warmed to room temperature. 5-bromoisobenzofuran-1(3H)-one (5.00 g, 23 mmol) was added in one portion and the reaction mixture was stirred for 2.5 hours and quenched with water. The mixture was filtered to remove the solid impurities, then the filtrate was washed with 0.5N aqueous HCl (100 mL) and brine (200 mL). The organic layer was dried with MgSO4, filtered, and concentrated to give a white solid. This was triturated with EtOAc and filtered to give 4-bromo-2-(hydroxymethyl)-N-methylbenzamide (3.34 g, 58% yield) as a white solid.

1. temperaturecooled to 0° C.
2. customresulting in the formation of a thick white slush
3. temperatureThis was warmed to room temperature
4. customquenched with water
5. filtrationThe mixture was filtered
6. customto remove the solid impurities
7. washthe filtrate was washed with 0.5N aqueous HCl (100 mL) and brine (200 mL)
8. dry with materialThe organic layer was dried with MgSO4
9. filtrationfiltered
10. concentrationconcentrated
11. customto give a white solid
12. customThis was triturated with EtOAc
13. filtrationfiltered

ORDレコード

ord-e46de78712e244f3b6ee3e8487298bb6

出典データセット

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08524900B2