Pyridine → 4-Nitrobenzyl bromoacetate

Participants

Reaction Steps

Bromoacetyl chloride (113 g) was dropwise added to a stirred solution of 4-nitrobenzyl alcohol (9.2 g) and pyridine (10 ml) in dry tetrahydrofuran (100 ml) at 0° C. over 50 minutes. The mixture was stirred at 0° to 5° C. for 30 minutes, and evaporated in vacuo. The residue was dissolved in a mixture of chloroform (70 ml) and water (20 ml), and then the organic layer was separated. The organic layer was washed with a diluted aqueous hydrochloric acid and water in turn, and then dried over anhydrous magnesium sulfate. The solution was evaporated in vacuo, and the residue was recrystallized from methanol to give crystals (6.74 g) of 4-nitrobenzyl bromoacetate.

Provenance & Evidence