Propanoic acid, 2-bromo-2-methyl-, ethyl ester → HCID 71739072, compound

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Reaction Steps

To a solution of 6-chloropyridin-3-ol (40 g, 309 mmol, Eq: 1.00) and ethyl 2-bromo-2-methylpropanoate (63.2 g, 48.1 ml, 324 mmol, Eq: 1.05) in 300 ml of CH3 CN was added Cs2 CO3 (216 g, 664 mmol, 309 mmol, Eq: 2.15) and the resulting reaction mixture was stirred under argon atmosphere for 48 h. The reaction mixture was filtered and the filtercake was washed well with EtOAc. The combined filtrate and washes were diluted with water (300 ml) and shaken and the organic phase was collected. The aqueous phase was back-extracted with EtOAc (2×150 ml). The combined organics were dried (MgSO4), filtered and concentrated in vacuo. Purification by passing through a plug of 200 g of silica and elution with 30% EtOAc/Hexanes afforded the desired product (51.1 g) as a light yellow oil. 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 1.27 (t, J=7.18 Hz, 3 H) 1.61 (s, 6 H) 4.24 (q, J=7.18 Hz, 2 H) 7.12-7.25 (m, 2 H) 8.01 (d, J=2.64 Hz, 1 H).

Provenance & Evidence