Boron Trichloride → 4-Methoxy-5-methyl-2-nitrophenol

Temperature

-20 °C

1-Methyl-2,5-bis(methyloxy)-4-nitrobenzene (3.96 g, 20 mmol) was dissolved in CH2Cl2 (20 mL) and cooled to −20° C. A solution of BCl3 (1.0 M) in CH2Cl2 (20 mL) was added to above solution drop wise over 5 minutes. A purple solution was obtained. The reaction mixture was slowly warmed to room temperature and stirred for 20 h. The mixture was then quenched with saturated Na2CO3, stirred for 10 minutes and then extracted with EtOAc (3×100 mL). The organic extracts were combined, washed with water, brine, and dried (Na2SO4). The solvent was removed via rotovap to give the title compound (3.65 g, 99%) as a yellow solid. MS (ES) m/e 184 [M+H]+.

1. customA purple solution was obtained
2. temperatureThe reaction mixture was slowly warmed to room temperature
3. customThe mixture was then quenched with saturated Na2CO3
4. stirringstirred for 10 minutes
5. extractionextracted with EtOAc (3×100 mL)
6. washwashed with water, brine
7. dry with materialdried (Na2SO4)
8. customThe solvent was removed via rotovap

ORD record

ord-edd55955f8b643e99ea96a7bbb044fd8

Source dataset

uspto-grants-2008_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07432258B2