반응 #1253204

반응 방정식

Phenylheptane

bromine

→

pure product

1-Bromo-4-heptylbenzene

용매

chloroform

반응 조건

후처리

1. 1
   기타the reaction was quenched with 1N KOH
2. 2
   추출After extraction
3. 3
   세척the organic phase was washed with water
4. 4
   건조dried over MgSO4
5. 5
   기타was purified by column chromatography on silica gel

실험 절차

Phenylheptane (100 g, 0.57 mol) was dissolved in 900 mL of chloroform, and ferric chloride (1.41 g, 9 mmol) was added. The mixture was cooled to 0° C. and bromine (32 mL, 0.62 mmol) was added dropwise through an additional funnel. The reaction was kept in dark to prevent the bromination of the aliphatic side chain. After stirring at room temperature overnight, the reaction was quenched with 1N KOH. After extraction, the organic phase was washed with water and dried over MgSO4. The crude product was a brown oil and was purified by column chromatography on silica gel using heptane as an eluent to give 60 g of pure product as light yellow oil at 42% yield. 1H NMR (CDCl3) δ (ppm): 0.88 (t, J=6.9 Hz, 3H), 1.26-1.31 (m, 8H), 1.54-1.59 (m, 2H), 2.54 (t, J=7.8 Hz, 2H), 7.04 (d, J=8.2 Hz, 2H), 7.38 (d, J=8.2 Hz, 2H). FD-MS: m/z 255 (M+).

출처