Reaktion #1253204

Reaktionsgleichung

Phenylheptane

bromine

→

pure product

1-Bromo-4-heptylbenzene

Lösungsmittel

chloroform

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe reaction was quenched with 1N KOH
2. 2
   ExtraktionAfter extraction
3. 3
   Waschenthe organic phase was washed with water
4. 4
   Trocknendried over MgSO4
5. 5
   Sonstigewas purified by column chromatography on silica gel

Vorschrift

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+).

Quelle