3-Pyridyl bromide

CLEAR COLOURLESS TO YELLOW LIQUID

Pyridine as novel substrate for regioselective oxygenation with aromatic peroxygenase from Agrocybe aegerita.

3-Bromopyridine undergoes lithiation with LDA at low temperatures in the 4-position: Heterocycles, involved in formation of the Grignard by Mg exchange with i-PrMgCl and in transmetallation of the lithiated derivative with zinc chloride followed by treatment with an electrophile as a route to 4-substituted 3-bromopyridines.

ChEBI: A monobromopyridine in which the bromo substituent is located at position 3.

Synthesis, p. 293, 1974 DOI: 10.1055/s-1974-23300

A method for synthesizing 3-bromopyridine, comprising the steps of:

Add 60 g of pyridine and 100 mL of water to a 500 mL three-necked flask, add 40% HBr (160 g, temperature control of 20-30 during the process of addition) dropwise with stirring, stirring after the dropwise addition until dissolved clear, to obtain the brominated reaction solution;

Heat the bromination reaction solution to 70 and slowly add 30% H2O280mL, drop process control temperature 70-80 (drop process slowly exothermic), drop after the completion of the temperature control 80 stirring reaction for 24 hours, to get the crude products;

_x000D

The crude product was cooled down to below 10, the pH was adjusted to pH=8 with 3N NaOH aqueous solution, ethyl acetate (350mL×3) was added to extract, and the organic phase was backwashed with aqueous sodium sulfite to obtain the extract (organic phase);

The extract (organic phase) was concentrated and then distilled under reduced pressure, that is, 31 g of 3-bromopyridine was obtained, and the GC purity was 85.1%.