ChemicalBook CAS DataBase List 3-(3'-TRIFLUOROMETHYL PHENYL) PROPANOL

3-(3'-TRIFLUOROMETHYL PHENYL) PROPANOL synthesis

12synthesis methods

Product Name:3-(3'-TRIFLUOROMETHYL PHENYL) PROPANOL
CAS Number:78573-45-2
Molecular formula:C10H11F3O
Molecular Weight:204.19

585-50-2 Synthesis

3-(3-Trifluoromethylphenyl)propionic acid

585-50-2
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78573-45-2
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$10.00/1g

Yield:78573-45-2 94%

Reaction Conditions:

Stage #1:3-(3-trifluoromethylphenyl)propanoic acid with borane-THF in tetrahydrofuran at 0 - 20; for 25 h;
Stage #2: with water in tetrahydrofuran;methanol

Steps:

3-(3-Trifluoromethyl-phenyl)-propionic acid (12.4 g, 57 mmol) was dissolved in THF (160 ml) in an inert atmosphere and cooled to 0° C. followed by slow addition of borane in THF (85 ml, 85 mmol). Stirring was continued at 0° C. for 1 h and at rt for 24 h. The mixture was cooled to 0° C. and methanol (100 ml) and water (100 ml) was carefully added. The organic solvents were removed under reduced pressure. The remaining aqueous layer was extracted with DCM (3*100 ml). The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by flash chromatography (silicagel, DCM/methanol=9/1) to give 10.97 g (94%) of 3-(3-trifluoromethyl-phenyl)-propan-1-ol. LC-MS: t_R=0.87 min; [M+H]⁺=no ionisation.

References:

Actelion Pharmaceuticals Ltd. US2009/99228, 2009, A1 Location in patent:Page/Page column 11; 18

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