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

5-Amino-2-trifluoromethoxybenzoic acid methyl ester (3.0 g, 12.8 mmol) was dissolved in THF (20 mL) in a three-necked flask equipped with a thermometer and an addition funnel under nitrogen. Under stirring and ice-cooling lithium aluminum hydride (1 M in THF, 15 mL) was added dropwise within 10 minutes. Stirring was continued at room temperature for 1 hr, and the reaction was concentrated in vacuo. The residue was suspended in DCM (150 mL) and water (50 mL), then filtered through celite, washed with DCM and water. The filtrate was separated, and the water phase was extracted once more with DCM (30 mL). 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-trifluoromethoxyphenyl)methanol.

1. customequipped with a thermometer and an addition funnel under nitrogen
2. additionwas added dropwise within 10 minutes
3. stirringStirring
4. concentrationthe reaction was concentrated in vacuo
5. filtrationwater (50 mL), then filtered through celite
6. washwashed with DCM and water
7. customThe filtrate was separated
8. extractionthe water phase was extracted once more with DCM (30 mL)
9. washThe combined organic phases were washed with water (2×20 mL)
10. dry with materialdried (magnesium sulphate)
11. concentrationconcentrated in vacuo

ORD record

ord-b2a0e0a3d99b48728d9ed78df70b7dad

Source dataset

uspto-grants-2003_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06562807B2