Sodium Dithionite → 4-Bromo-2-(2,2-dimethoxyethyl)aniline

Compound 66 (75 mg, 0.259 mmol) was dissolved in anhydrous ethanol (10 mL) in a dry argon purged flask fitted with a magnetic stir bar and condenser. Sodium dithionite (158.8 mg, 0.776 mmol) and sodium bicarbonate (130.6 mg, 1.554 mmol) are added to the flask and mixture heated to reflux for 24 hours. After cooling to room temperature, the reaction was quenched by the addition of H2O (10 mL) and the ethanol removed under reduced pressure. The resulting aqueous layer was transferred to a separatory funnel and extracted with ethyl acetate (three times). The combined organic layers were washed with brine, dried over sodium sulphate, filtered, concentrated and the residue purified via chromatography on silica gel (methanol:CH2Cl2, 2:98) to yield a brown oil, 67 (32 mg, 47.5%). 1H NMR (CDCl3) δ 2.83 (d, 2H, J=5.3 Hz), 3.38 (s, 6H), 4.48 (t, 1H, J=5.3 Hz), 6.61 (d, 1H, J=8.2 Hz), 7.13 (d, 1H, J=2.2 Hz), 7.15-7.17 (m, 1H); ESI-MS (m/z, %): 198/200 (M+−2MeO, 100%).

1. customfitted with a magnetic stir bar and condenser
2. temperatureheated
3. temperatureto reflux for 24 hours
4. customthe reaction was quenched by the addition of H2O (10 mL)
5. customthe ethanol removed under reduced pressure
6. customThe resulting aqueous layer was transferred to a separatory funnel
7. extractionextracted with ethyl acetate (three times)
8. washThe combined organic layers were washed with brine
9. dry with materialdried over sodium sulphate
10. filtrationfiltered
11. concentrationconcentrated
12. customthe residue purified via chromatography on silica gel (methanol:CH2Cl2, 2:98)

ORDレコード

ord-945e3c0d470244abbf24c862108876e9

出典データセット

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07989447B2