반응 #43290

반응 방정식

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

N-bromosuccinimide

AIBN

→

light yellow solid

수율 37.0%

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

수율 37.0%

용매

CCl4

CCl4

반응 조건

후처리

1. 1
   온도the reaction was heated
2. 2
   온도to reflux for 1 h
3. 3
   기타to irradiate the refluxing solution for an additional 4 h
4. 4
   세척washed with water twice (150 mL), saturated brine
5. 5
   건조the organic layer was dried (anhydrous Na2SO4)
6. 6
   기타the solvents removed at reduced pressure

실험 절차

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).

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