2-Bromo-4-nitroanisole → 3-Bromo-4-methoxyaniline

Temperatur

70 °C

Stannous chloride (96.839 g, 5.0 eq.) was added to a solution of 2-bromo-4-nitroanisole (23.7 g, 1.0 eq.) in ethanol (250 mL) and the mixture was stirred at 70° C. for 2 h, partitioned between ethyl acetate and sodium bicarbonate solution 10%. The pH was adjusted to 9 with 1N sodium hydroxide solution and the aqueous layer was extracted twice with ethyl acetate. The combined organic fractions were washed with water and brine, dried over magnesium sulfate, filtered, evaporated to dryness and purified on silica gel, eluting with hexane/ethyl acetate 1:1, to yield 13.82 g (67%) from the desired product as light brown solid. MS (m/e): 204.1 (MH+, 100%).

1. custompartitioned between ethyl acetate and sodium bicarbonate solution 10%
2. extractionthe aqueous layer was extracted twice with ethyl acetate
3. washThe combined organic fractions were washed with water and brine
4. dry with materialdried over magnesium sulfate
5. filtrationfiltered
6. customevaporated to dryness
7. custompurified on silica gel
8. washeluting with hexane/ethyl acetate 1:1

ORD-Eintrag

ord-f39bf865ebcb4bb39f868cb4430bed9f

Quelldatensatz

uspto-grants-2010_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07745479B2