Reaction #324445

Reaction equation

H2O

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

Cs2CO3

bromophenylacetic acid methyl ester

→

title compound

Yield 96.5%

3-[5-Chloro-2-(methoxycarbonyl-phenyl-methoxy)-phenoxy]-azetidine-1-carboxylic acid tert-butyl ester

Yield 96.5%

Solvents

DMF

Conditions

Workup

1. 1
   Extractionthe mixture extracted with EtOAc (2×)
2. 2
   WashThe combined organics were washed with brine
3. 3
   Otherdried

Procedure

To 3-(5-Chloro-2-hydroxy-phenoxy)-azetidine-1-carboxylic acid tert-butyl ester (1.1 g, 3.7 mmol) in DMF (18 mL) was added Cs2CO3 (1.5 g, 4.4 mmol) and bromophenylacetic acid methyl ester (0.92 g, 0.63 mL, 4.0 mmol). After 15 h, H2O was added and the mixture extracted with EtOAc (2×). The combined organics were washed with brine and dried. Silica gel chromatography (5-25% EtOAc in hexanes) gave 1.6 g (96%) of the title compound. 1H NMR (CDCl3): 7.55-7.33 (m, 2H), 7.43-7.36 (m, 3H), 6.85 (d, J=1.2, 2H), 6.51 (t, J=1.2 Hz, 1H), 5.58 (s, 1H), 4.91-4.85 (m, 1H), 4.31-4.26 (m, 2H), 3.98-3.93 (m, 2H), 3.89-3.74 (m, 3H), 1.46 (s, 9H).

Source