Allyl bromide → 2-[(2-Propenyloxy)-methyl]-5-nitrobenzenamine

Temperature

0 °C

A stirred solution of 2-amino-4-nitrobenzenemethanol (14.3 g, 85 mmol) in dry THF (350 mL) at 0° C. under an argon atmosphere, is treated dropwise over 35 min with a solution of potassium tert-butylate in THF (Fluka; 85 mL of 1.0 M). The mixture is stirred at 0° C. for 15 min and then treated dropwise over 50 min with a solution of allylbromide (7.9 mL, 94 mmol) in dry THF (80 mL) at 0° C. and then stirred at 20° C. for 90 min. The mixture is diluted with ethyl acetate (800 mL). The resulting solution is washed with saturated aqueous ammonium chloride (3×400 mL), dried (MgSO4), filtered and the solvent is evaporated off under reduced pressure to yield the crude product which is purified by column chromatography on silica gel, eluent 50% ethyl acetate in hexane, to give the title compound as a brown oil.

1. stirringstirred at 20° C. for 90 min
2. washThe resulting solution is washed with saturated aqueous ammonium chloride (3×400 mL)
3. dry with materialdried (MgSO4)
4. filtrationfiltered
5. customthe solvent is evaporated off under reduced pressure
6. customto yield the crude product which
7. customis purified by column chromatography on silica gel, eluent 50% ethyl acetate in hexane

ORD record

ord-3368b4e0080f4501b090a6f926e165fa

Source dataset

uspto-grants-2009_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07557105B2