Heptylbenzene → 1-Bromo-4-heptylbenzene

HRID 1166022Notes

Reaction equation

HRID 1166022 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:14]Br>C(Cl)(Cl)Cl>[Br:14][C:4]1[CH:5]=[CH:6][C:1]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])=[CH:2][CH:3]=1

Participants

4

Reactant 2

HCID 14115HeptylbenzeneHCID 24408Bromine

Product 1

HCID 27751001-Bromo-4-heptylbenzeneYield 37,921.801%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

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+).

Workup

  1. customthe reaction was quenched with 1N KOH
  2. extractionAfter extraction
  3. washthe organic phase was washed with water
  4. dry with materialdried over MgSO4
  5. customwas purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-a6d5cc91630245bc8804d18c7cc538b6
Source dataset
uspto-grants-2003_09
Patent number
US06613457B2

Reaction notes

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