ChemicalBook CAS DataBase List 2-Bromopyridine-5-carbaldehyde

2-Bromopyridine-5-carbaldehyde synthesis

12synthesis methods

Product Name:2-Bromopyridine-5-carbaldehyde
CAS Number:149806-06-4
Molecular formula:C6H4BrNO
Molecular Weight:186.01

154321-32-1

149806-06-4

General procedure for the synthesis of 2-bromo-5-formylpyridine (Intermediate 1b) from 2-bromo-5-(dibromomethyl)pyridine (Intermediate Ia, 3.650 g, 11.07 mmol): a mixture of Intermediate Ia with calcium carbonate (2.437 g, 24.35 mmol) in water (80 ml) was stirred and reacted for 16 hours at 105 °C. After completion of the reaction, the mixture was cooled to room temperature, diluted with water and extracted twice with ethyl acetate (EtOAc). The organic phases were combined, washed sequentially with water and saturated sodium chloride (NaCl) solution, dried over anhydrous magnesium sulfate (MgSO4), filtered and concentrated under reduced pressure to give Intermediate 1b (1.890 g, 92% yield). The product was characterized by 1H NMR (500 MHz, CDCl3): δ 10.05 (s, 1H), 8.78 (d, J = 2.2 Hz, 1H), 7.98 (dd, J = 8.2,2.4 Hz, 1H), 7.65 (d, J = 8.2 Hz, 1H).

154321-32-1
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149806-06-4
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Yield:149806-06-4 92%

Reaction Conditions:

with calcium carbonate in water at 105; for 16 h;

Steps:

A.1 Preparation of 6-bromonicotinaldehyde (Ib)
A solution of intermediate Ia (3.650 g, 11.07 mmol), calcium carbonate (2.437 g,24.35 mmol) in water (80m1) was stirred at 105°C for 16 hours. The cooled mixture was diluted with water and extracted with EtOAc twice. The combined organics were washed with water, with saturated solution of NaC1, dried over MgSO4, filtered and evaporated to give intermediate lb (1.890 g, 92%). ‘H NMR (500 MHz, CDC13) ? 10.05 (s, 1H), 8.78(d, J= 2.2 Hz, 1H), 7.98 (dd, J= 8.2, 2.4 Hz, 1H), 7.65 (d, J= 8.2 Hz, 1H).

References:

AB SCIENCE;MOUSSY, Alain;BENJAHAD, Abdellah;PEZ, Didier;SANDRINELLI, Franck;MARTIN, Jason;PICOUL, Willy;CHEVENIER, Emmanuel WO2016/124747, 2016, A1 Location in patent:Page/Page column 58; 59

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