Yield:197783-88-3 77%

Reaction Conditions:

with lithium aluminium tetrahydride in tetrahydrofuran at 0 - 20; for 4 h;Inert atmosphere;

Steps:

35 5.1.23 2-Amino-6-fluorobenzyl alcohol (2a)

General procedure: To a stirred suspension of LiAlH₄ (740 mg, 19.5 mmol) in THF (20 mL) was added a solution of 6-fluoroanthranilic acid (1.01 g, 6.51 mmol) in THF (10 mL) at 0 °C under an Ar atmosphere and stirred at rt. After 4 h with stirring, AcOEt and saturated Na₂SO₄ aqueous solution were added to the solution. The resulting solid was removed by filtration and the obtained filtrate was basified (pH 9) with saturated NaHCO₃ aqueous solution, and extracted with AcOEt three times. The combined organic extracts were washed with brine, dried over Na₂SO₄, and evaporated in vacuo. The crude compound was chromatographed on silica gel, but not purified completely. The resulting compound 2a was used for the next reaction without further purification.

References:

Ida, Yoshihiro;Matsubara, Ayaka;Nemoto, Toru;Saito, Manabu;Hirayama, Shigeto;Fujii, Hideaki;Nagase, Hiroshi [Bioorganic and Medicinal Chemistry,2012,vol. 20,# 19,p. 5810 - 5831]