Synthesis
GENERAL PROCEDURE: A solution was prepared by dissolving 2-amino-5-chlorobenzoic acid (8.5 mmol) in THF (24 mL) at room temperature. This solution was added dropwise to a suspension of lithium aluminum hydride (20.4 mmol) in THF (10 mL) over 20 minutes. The reaction mixture was stirred continuously for 3.5 h at room temperature. Subsequently, water (10 mL) was added slowly at 0 °C to quench the reaction. The resulting suspension was filtered through a diatomaceous earth plug and washed with EtOAc (100 mL). The organic phase was washed with brine (30 mL), dried over anhydrous MgSO4 and finally concentrated under vacuum to give 2-amino-5-chlorobenzyl alcohol.
References
[1] ACS Catalysis, 2013, vol. 3, # 4, p. 622 - 624
[2] Organic Letters, 2017, vol. 19, # 12, p. 3219 - 3222
[3] Tetrahedron Letters, 2017, vol. 58, # 40, p. 3795 - 3799
[4] Patent: WO2010/37533, 2010, A1. Location in patent: Page/Page column 44
[5] Organic Letters, 2016, vol. 18, # 21, p. 5572 - 5575
