Reaction #43290

Reaction equation

acetic acid 2-(6-methyl-2-nitro-pyridin-3-yloxy)-ethyl ester

N-bromosuccinimide

AIBN

→

light yellow solid

Yield 37.0%

Acetic Acid 2-(6-bromomethyl-2-nitro-pyridin-3-yloxy)-ethyl ester

Yield 37.0%

Solvents

CCl4

CCl4

Conditions

Workup

1. 1
   Temperaturethe reaction was heated
2. 2
   Temperatureto reflux for 1 h
3. 3
   Otherto irradiate the refluxing solution for an additional 4 h
4. 4
   Washwashed with water twice (150 mL), saturated brine
5. 5
   Dryingthe organic layer was dried (anhydrous Na2SO4)
6. 6
   Otherthe solvents removed at reduced pressure

Procedure

To a solution of 2.16 gm (9.0 mmol) of acetic acid 2-(6-methyl-2-nitro-pyridin-3-yloxy)-ethyl ester 94, 1.76 gm (9.9 mmol) of N-bromosuccinimide in 125 mL of CCl4 was added 0.074 gm (44.9 μmol) of AIBN and the reaction was heated to reflux for 1 h. After 1 h a 500 watt sun lamp was used to irradiate the refluxing solution for an additional 4 h. The mixture was poured into 300 mL of CCl4 and washed with water twice (150 mL), saturated brine and the organic layer was dried (anhydrous Na2SO4) and the solvents removed at reduced pressure. Column chromatography of the residue using 50%-30%-10% CH2Cl2-hexanes yielded 1.06 gm (37%) of a light yellow solid. 1H NMR (400 MHz, CDCl3) δ: 2.06 (s, 3H), 4.31 (t, 2H, J=4.1 Hz), 4.41 (t, 2H, J=4.1 Hz), 4.48 (s, 2H), 7.49 (d, 2H, J=8.5 Hz), 7.65 (d, 2H J=8.5 Hz).

Source