Reaction #955918

Reaction equation

2-(2-hydroxyethyl)pyridine

HBr

→

solid

Yield 73.0%

2-(2-bromoethyl)pyridinium bromide

Yield 73.0%

Solvents

acetic acid

Conditions

Workup

1. 1
   OtherThe reaction was evaporated under high vacuum
2. 2
   Otherto produce a brown solid
3. 3
   OtherThe solid was re-crystallized from hot isopropanol

Procedure

To a solution of 2-(2-hydroxyethyl)pyridine (3 ml, 26.6 mmol) was added 30 ml of 33% HBr in acetic acid. The yellow solution was heated in the capped vial at 78° C. for 2 days. The reaction was evaporated under high vacuum to produce a brown solid. The solid was re-crystallized from hot isopropanol to produce a light tan solid (73%). 1H NMR (500 MHz, dMSO): δ 3.62-3.65 (t, 2H), 3.95-3.98 (t, 2H), 7.95 (t,1H), 8.09-8.10 (d, 1H), 8.58 (t, 1H), 8.90 (d, 1H).

Source