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 (1M 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 dichloromethane (150 mL) and water (50 mL), then filtered through celite, washed with dichloromethane and water. The filtrate was separated, and the water phase was extracted once more with dichloromethane (30 mL). The combined organic phases were washed with water (2×20 mL), dried (MgSO4) 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 dichloromethane and water
7. customThe filtrate was separated
8. extractionthe water phase was extracted once more with dichloromethane (30 mL)
9. washThe combined organic phases were washed with water (2×20 mL)
10. dry with materialdried (MgSO4)
11. concentrationconcentrated in vacuo

ORD record

ord-748f357d6c1347eabb418800da46ce49

Source dataset

uspto-grants-2003_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06503949B1