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0 °C

3-(Methoxycarbonyl)-5-nitrobenzoic acid (20.0 g, 88.9 mmol) was combined with tetrahydrofuran (150 mL) and cooled to 0° C. To this solution was added a 1 M borane tetrahydrofuran complex (178 mL, 178 mmol) cautiously over 15 min and the reaction mixture allowed to warm to room temperature overnight. The mixture was cooled to 0° C., treated with excess methanol and concentrated in vacuo to afford to afford a precipitate which was dissolved in ethyl acetate, washed with concentrated sodium bicarbonate (2×), then brine (2×), dried over sodium sulfate, and concentrated to afford 18.2 g (97%) which was used without further purification. 1H-NMR (CDCl3, 300 MHz) δ 8.70 (s, 1H), 8.39 (s, 1H), 8.30 (s, 1H), 4.84 (s, 2H), 3.95 (s, 3H). Mass spec.: 212.06 (MH)+.

1. additionTo this solution was added a 1 M borane tetrahydrofuran complex (178 mL, 178 mmol) cautiously over 15 min
2. temperatureto warm to room temperature overnight
3. temperatureThe mixture was cooled to 0° C.
4. concentrationconcentrated in vacuo
5. customto afford
6. customto afford a precipitate which
7. washwashed with concentrated sodium bicarbonate (2×)
8. dry with materialbrine (2×), dried over sodium sulfate
9. concentrationconcentrated
10. customto afford 18.2 g (97%) which
11. customwas used without further purification