反応 #338683

反応方程式

4-bromo-1-methoxy-2-nitrobenzene

acetic acid

→

5-bromo-2-methoxyaniline

収率 76.7%

溶媒

water

反応条件

後処理

1. 1
   温度The mixture was cooled to ambient temperature
2. 2
   抽出the mixture was extracted with ethyl acetate (3×25 ml)
3. 3
   洗浄The combined organic extracts were washed with saturated aqueous sodium bicarbonate (3×25 ml)
4. 4
   乾燥The organic solution was dried over magnesium sulfate
5. 5
   ろ過filtered
6. 6
   その他the filtrate evaporated under reduced pressure
7. 7
   その他to give a residue
8. 8
   その他Purification of the material by flash chromatography on silica gel

実験手順

A mixture of 4-bromo-1-methoxy-2-nitrobenzene (3.0 g, 12.9 mmol) and glacial acetic acid (25 ml) was heated at 100° C. under an atmosphere of nitrogen. Iron powder (2.2 g, 38.8 mmol) was added and the mixture was stirred for one hour at a temperature of 100° C. The mixture was cooled to ambient temperature then water (100 ml) was added and the mixture was extracted with ethyl acetate (3×25 ml). The combined organic extracts were washed with saturated aqueous sodium bicarbonate (3×25 ml) and then brine. The organic solution was dried over magnesium sulfate filtered and the filtrate evaporated under reduced pressure to give a residue. Purification of the material by flash chromatography on silica gel using heptane/ethyl acetate (6:4) as an eluent yielded 5-bromo-2-methoxyaniline (2.0 g): 1H NMR (DMSO-d6, 400 MHz) 6.76 (s, 1H), 6.71 (d, 1H), 6.61 (d, 1H), 4.99 (bs, 2H), 3.74 (s, 3H); (TLC (heptane/ethyl acetate 1:1) Rf 0.5; RP-HPLC (Hypersil HyPurity Elite C18, 5 m, 200 A, 250×4.6 mm; 25-100% acetonitrile-0.1 M ammonium acetate over 25 min, 1 ml/min) tr=13.33 min.; MS: MH+443.

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