1-BROMO-4-DECYLBENZENE

The product was obtained using a Wolff–Kishner reaction to reduce 1-(4-bromophenyl)decan-1-one 7. 1-(4-Bromophenyl)decan-1-one 7 (1.3g, 4.2mmol), hydrazine monohydrate (1.2mL, 16mmol) and KOH (1.8g, 32mmol) were dissolved in 25mL of 1-octanol to yield a green suspension in a two-necked 50mL flask. The reaction mixture was stirred at reflux at 135°C for 2h to give an almost colorless solution. The reaction mixture was then cooled to room temperature and diluted with ether (50mL), washed with 1N aqueous HCl (50mL), 2N aqueous HCl (20mL), brine (2 times, 30mL), dried over MgSOGeneral procedure: To a solution of NaOH (32 mg, 0.8 mmol, 1.6 equiv), catalyst 1 (8.4mg, 0.025 mmol, 5 molpercent), NaI (37 mg, 0.25 mmol, 0.5 equiv), and i-PrOH (76 μL, 1 mmol, 2 equiv) in dry 1, 4-dioxane (2.4 mL), were added alkyl halide (0.5 mmol) and the alkyl-(9-BBN) (1.6 mL, 0.8mmol, 1.6 equiv) under a NThe product was obtained using a Wolff-Kishner reaction to reduce 1-(4-bromophenyl)decan-1-one 7. 1-(4-Bromophenyl)decan-1-one 7 (1.3g, 4.2mmol), hydrazine monohydrate (1.2mL, 16mmol) and KOH (1.8g, 32mmol) were dissolved in 25mL of 1-octanol to yield a green suspension in a two-necked 50mL flask. The reaction mixture was stirred at reflux at 135C for 2h to give an almost colorless solution. The reaction mixture was then cooled to room temperature and diluted with ether (50mL), washed with 1N aqueous HCl (50mL), 2N aqueous HCl (20mL), brine (2 times, 30mL), dried over MgSO4, filtered, concentrated in vacuo. 1-Octanol was removed by vacuum distillation to yield about 2.7g of the crude product. The product was purified using column chromatography with heptane as eluent. Yield 40%. Colorless oil. Rf=0.61 (100% heptane). 1H NMR (500MHz, CDCl3) delta 7.37 (d, J=8.3, 2H), 7.03 (d, J=8.1, 2H), 2.54 (t, J=7.7, 2H), 1.60-1.54 (m, 2H), 1.28-1.25 (m, 14H), 0.88 (t, J=6.8, 3H).13C NMR (50MHz, CDCl3) delta 142.05, 131.46, 130.37, 119.47, 35.59, 32.14, 31.56, 29.85, 29.82, 29.71, 29.57, 29.43, 22.93, 14.34. MS (APPI): m/z 296.2 [M+].

Molecular Weight:297.27
XLogP3:7.5
Rotatable Bond Count:9
Exact Mass:296.11396
Monoisotopic Mass:296.11396
Heavy Atom Count:17
Complexity:159
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes