3-amino-1-(2-fluorophenyl)propan-1-ol synthesis
- Product Name:3-amino-1-(2-fluorophenyl)propan-1-ol
- CAS Number:1225519-67-4
- Molecular formula:C9H12FNO
- Molecular Weight:169.1961
106468-02-4
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Yield:1225519-67-4 82%
Reaction Conditions:
with borane-THF in tetrahydrofuran at 75; for 2 h;
Steps:
6
3-Amino-1-(2-fluoro-phenyl)-propan-1-ol. (0211) To a stirring solution of (2-fluoro-phenyl)-hydroxy-acetonitrile (5 g, 30.2 mmol) in tetrahydrofuran (20 mL) was slowly added a solution of borane-tetrahydrofuran complex (67 mL, 67.0 mmol, 1M in tetrahydrofuran). After bubbling ceased, the reaction mixture was heated to 75° C. for 2 hours and then allowed to cool to ambient temperature and concentrated. Methanol (30 mL) was added dropwise followed by hydrogen chloride (33 mL, 133 mmol, 4N in 1,4-dioxane). The resulting mixture was heated to reflux for 2 hours, allowed to cool to ambient temperature and then concentrated at reduced pressure. To the residue was added aqueous hydrochloric acid (10 mL, 1 N) followed by ethyl acetate (30 mL). The layers were separated and the aqueous layer was basified with sodium carbonate until pH>10 and this aqueous phase was mixed with brine (40 mL) and extracted dichloromethane (3×75 mL). The organic extracts were combined, dried (anhydrous magnesium sulfate) and concentrated at reduced pressure to give the product as a colorless oil (4.2 g, 82%).
References:
US8609849,2013,B1 Location in patent:Page/Page column 27
31915-26-1
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446-52-6
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