1-butyl-4-chlorobenzene

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 250 ml round-bottomed flask were added 5.0 g (29.65 mmol) 4-chlorophenylbutane and 10 ml 1,2-dichloroethane. To the stirred solution was added a solution of 4.35 g (32.62 mmol) aluminum chloride and 4.22 ml (59.31 mmol) acetyl chloride in 50 ml 1,2-dichloroethane. The solution evolved HCl as it was stirred at room temperature for 1 hour. It was then poured into water, the layers were separated, and the organic layer was washed with 1N HCl, aqueous sodium bicarbonate solution, and brine, dried over sodium sulfate, and evaporated to an oil, 6.7 g (>100%). NMR (CDCl3): 1.76 (m, 4H), 2.54 (m, 3H), 2.66 (m, 2H), 3.50 (m, 2H), 7.2 and 7.85 (m, 4H). IR (cm.-1, neat): 1678 (C=O). the layers were separated the organic layer was washed with 1N HCl, aqueous sodium bicarbonate solution, and brine dried over sodium sulfate evaporated to an oil, 6.7 g (>100%)

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 2.00 g (13.61 mmoles) of p-dichlorobenzene, and 0.050 g of [NiCltriphos]PF6 in 20 mL of ether at -78° C. was added 7.0 mL (14 mmoles) of 2M nBuMgCl in ether. After refluxing overnight and workup with NH4Cl solution, the residue (602 mg of 1.698 g) was flash-chromatographed with 5% EtOAc/hexane on silica gel to give 542 mg (67%) of 1-butyl-4-chlorobenzene. 1H NMR (200 MHz, CDCl3): δ7.22 (m,2H), 7.05 (m,2H), 2.59 (t, J=5.5 Hz, 2H), 1.58 (m, 2H), 1.34 (m,2H) 0.95 (t, J=5.2 Hz, 3H). IR(neat): 2958s, 2930s, 2859s, 1492s, 1466m, 1407m, 1901s, 1016s cm-1. After refluxing overnight workup with NH4Cl solution, the residue (602 mg of 1.698 g) was flash-chromatographed with 5% EtOAc/hexane on silica gel

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 250 ml round-bottomed flask were added 5.0 g (29.65 mmol) 4-chlorophenylbutane and 10 ml 1,2-dichloroethane. To the stirred solution was added a solution of 4.35 g (32.62 mmol) aluminum chloride and 4.22 ml (59.31 mmol) acetyl chloride in 50 ml 1,2-dichloroethane. The solution evolved HCl as it was stirred at room temperature for 1 hour. It was then poured into water, the layers were separated, and the organic layer was washed with 1N HCl, aqueous sodium bicarbonate solution, and brine, dried over sodium sulfate, and evaporated to an oil, 6.7 g (>100%). NMR (CDCl3): 1.76 (m, 4H), 2.54 (m, 3H), 2.66 (m, 2H), 3.50 (m, 2H), 7.2 and 7.85 (m, 4H). IR (cm.-1, neat): 1678 (C=O). the layers were separated the organic layer was washed with 1N HCl, aqueous sodium bicarbonate solution, and brine dried over sodium sulfate evaporated to an oil, 6.7 g (>100%)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 250 ml round-bottomed flask were added 5.0 g (29.65 mmol) 4-chlorophenylbutane and 10 ml 1,2-dichloroethane. To the stirred solution was added a solution of 4.35 g (32.62 mmol) aluminum chloride and 4.22 ml (59.31 mmol) acetyl chloride in 50 ml 1,2-dichloroethane. The solution evolved HCl as it was stirred at room temperature for 1 hour. It was then poured into water, the layers were separated, and the organic layer was washed with 1N HCl, aqueous sodium bicarbonate solution, and brine, dried over sodium sulfate, and evaporated to an oil, 6.7 g (>100%). NMR (CDCl3): 1.76 (m, 4H), 2.54 (m, 3H), 2.66 (m, 2H), 3.50 (m, 2H), 7.2 and 7.85 (m, 4H). IR (cm.-1, neat): 1678 (C=O). the layers were separated the organic layer was washed with 1N HCl, aqueous sodium bicarbonate solution, and brine dried over sodium sulfate evaporated to an oil, 6.7 g (>100%)

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Using a THF solution of 4-fluorophenylmagnesium bromide (1.46 mL, 1.03 M, 1.5 mmol), 4-butylchlorobenzene (168.7 mg, 1.0 mmol), FeF3.3H2O (8.34 mg, 0.05 mmol), 1,3-bis(2,6-diisopropylphenyl)imidazolinium chloride (63.8 mg, 0.15 mmol) and triphenylphosphine (13.1 mg, 0.05 mmol) as starting materials, the reaction was performed at a scale of 1.0 mmol at 60° C. for 24 hours, then at 80° C. for 12 hours in the same manner as in Example 15. After performing silica gel chromatography (pentane), the above compound was obtained as a white solid (0.201 g, yield=88%, purity=>98% (GC analysis)). at 80° C. for 12 hours in the same manner as in Example 15 the above compound was obtained as a white solid (0.201 g, yield=88%, purity=>98% (GC analysis))