Reaction #324442

Reaction equation

3-(5-Chloro-2-hydroxy-phenoxy)-azetidine-1-carboxylic acid tert-butyl ester

HCl

→

2-(azetidin-3-yloxy)-4-chloro-phenol hydrochloride

Solvents

EtOAc

dioxane

EtOAc

Conditions

Workup

1. 1
   Filtrationthe resulting white solid filtered

Procedure

To 3-(5-Chloro-2-hydroxy-phenoxy)-azetidine-1-carboxylic acid tert-butyl ester (0.80 g, 2.7 mmol) in EtOAc (2 mL) was added 4M HCl in dioxane (5 mL). After 18 h, EtOAc was added and the resulting white solid filtered to give 2-(azetidin-3-yloxy)-4-chloro-phenol hydrochloride as a white solid. To a CH2Cl2 (25 mL) solution of this compound was added Et3N (0.30 g, 0.42 mL, 3.0 mmol) and TFAA (0.58 g, 0.38 mL, 2.8 mmol). After 18 h, H2O was added and the reaction extracted with CH2Cl2 (2×). The combined organics were dried and concentrated to give 0.54 g (74% yield 2 steps) of the title compound as a brown oil that was used in the next step without further purification.

Source