Ammonium Chloride → (4-Bromo-2-chloro-phenyl)-(2-methyl-5-nitro-phenyl)-methanone

温度

-60 °C

The reaction was run under an argon atmosphere using dry glassware. 4-Bromo-2-chloroiodobenzene (25.5 g, 80.9 mmol) was dissolved in dry THF (400 mL) and cooled to −60° C. Isopropylmagnesium chloride (2 M in THF, 40.4 mL, 80.9 mmol) was added under stirring during 30 minutes. The reaction mixture was allowed to warm up to −40° C. and the mixture was stirred at −40° C. for 4 h. Compound 491 (22.2 g, 80.9 mmol) was added and the mixture was stirred at −40° C. for 3 h after which it was allowed to warm to room temperature and stirred for 17 h. A saturated aqueous solution of NH4Cl (200 mL) was added and the mixture was stirred for 1 h. The phases were separated and the aqueous phase was extracted with Et2O (4×100 mL). The combined organic phases were washed with brine, dried (MgSO4), filtered and concentrated in vacuo. The crude product was purified by flash chromatography using CH2Cl2/petroleum ether (40-60) 2:3 as the eluent to afford the title compound as yellow crystalline compound.

1. customusing dry glassware
2. temperatureto warm up to −40° C.
3. stirringthe mixture was stirred at −40° C. for 4 h
4. stirringthe mixture was stirred at −40° C. for 3 h after which it
5. temperatureto warm to room temperature
6. stirringstirred for 17 h
7. stirringthe mixture was stirred for 1 h
8. customThe phases were separated
9. extractionthe aqueous phase was extracted with Et2O (4×100 mL)
10. washThe combined organic phases were washed with brine
11. dry with materialdried (MgSO4)
12. filtrationfiltered
13. concentrationconcentrated in vacuo
14. customThe crude product was purified by flash chromatography

ORDレコード

ord-1fd89c9b113d4cbb84f4155130ecafd7

出典データセット

uspto-grants-2011_07

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07977387B2