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0 °C

A portion of lithium borohydride (0.458 g, 21.0 mmol) was diluted with THF (30 mL) followed by the dropwise addition of chlorotrimethylsilane (5.34 ml, 42.1 mmol). After stirring for 15 minutes, argon was bubbled through the reaction mixture for 2 minutes to eliminate trimethylsilane present in the reaction. (E)-2-methoxy-1-(2-nitrovinyl)-4-(trifluoromethyl)benzene (1.3 g, 5.26 mmol) was added portionwise (gas evolution occurred). The reaction was heated to reflux for 2 hours, cooled to 0° C. and carefully quenched with methanol (8 mL). The reaction mixture was concentrated, diluted with dichloromethane and 20% aqueous KOH. The layers were separated and the organic layer was dried over sodium sulfate, filtered and concentrated to yield 2-(2-methoxy-4-(trifluoromethyl)phenyl)ethanamine (1.1 g, 5.02 mmol, 95.4% yield).

1. customargon was bubbled through the reaction mixture for 2 minutes
2. customin the reaction
3. temperatureThe reaction was heated
4. temperatureto reflux for 2 hours
5. customcarefully quenched with methanol (8 mL)
6. concentrationThe reaction mixture was concentrated
7. additiondiluted with dichloromethane and 20% aqueous KOH
8. customThe layers were separated
9. dry with materialthe organic layer was dried over sodium sulfate
10. filtrationfiltered
11. concentrationconcentrated