Aluminium lithium hydride → (5-Amino-2-trifluoromethoxy-phenyl)-methanol

5-Amino-2-trifluoromethoxybenzoic acid methyl ester (3.0 g, 12.8 mmol) was dissolved under nitrogen in THF (20 mL) in a three-necked flask equipped with a thermometer and a separatory funnel. With stirring and ice-cooling lithium aluminium hydride (1 M in THF, 15 mL) was added dropwise over 10 min. Stirring was continued at room temperature for 1 hour, and the reaction mixture was concentrated in vacuo. The residue was suspended in DCM (150 mL) and water (50 mL), and filtered through celite. The filtrate was partitioned between DCM and water. The combined organic phases were washed with water (2×20 mL), dried (magnesium sulphate) and concentrated in vacuo to give 2.47 g of (5-amino-2-trifluoromethoxy-phenyl)methanol

1. customequipped with a thermometer and a separatory funnel
2. additionwas added dropwise over 10 min
3. stirringStirring
4. concentrationthe reaction mixture was concentrated in vacuo
5. filtrationwater (50 mL), and filtered through celite
6. customThe filtrate was partitioned between DCM and water
7. washThe combined organic phases were washed with water (2×20 mL)
8. dry with materialdried (magnesium sulphate)
9. concentrationconcentrated in vacuo

ORD record

ord-2506a64631ae49a6a440415ec469d7d9

Source dataset

uspto-grants-2003_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06562807B2