Aluminium lithium hydride → (4-Amino-2-fluorophenyl)methanol

Participants

Reaction Conditions

Reaction Steps

To a 250 ml three necked round bottom flask, methyl 4-amino-2-fluorobenzoate (2.75 g, 0.0162 mole) was added in anhydrous THF (60 ml) under nitrogen atmosphere and cooled to 0-5° C. After 15 minutes, 2.0 M solutions of LAH in THF (24.3 ml, 0.0487 mole) was added dropwise and stirred for 10 min. The reaction mixture was allowed to warm up to room temperature and stirred at same temperature for 1 hr. After completion of the reaction, the reaction mixture was cooled to 5° C. and quenched with sat. NH4Cl (25 ml) and diluted with water (100 ml) followed by extraction with ethyl acetate. The combined organics were washed with water, dried over sodium sulphate and evaporated to afford brown solid (crude) product which was purified using column purification by eluting the compound with 20% ethyl acetate in hexanes to yield 1.7 g of (4-amino-2-fluorophenyl)methanol.

Provenance & Evidence