1-Cyclopropylnaphthalene

Cyclopropylmagnesium bromide (15OmL, 0.5M in tetrahydrofuran) was slowly added to a solution of 1 -bromonaphthalene (1Og, 50mmol) and [l , 3-bis(diphenylphosphino)ρroρane] dichloro nickel (II) in tetrahydrofuran (1OmL) stirred at 0°C, and the reaction mixture stirred at room temperature for 16 hours. The solvent was removed under reduced pressure and ethyl acetate and aqueous ammonium chloride were added- After extraction, the organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography to yield l-cyclopropylnaphthalcne (6.4g, 76percent).Cyclopropylmagnesium bromide (150 niL, 0.5 M in tetrahydrofuran) was slowly added to a solution of 1-bromo-naphthalene (10 g, 50 mmol) and [1, 3- bis(diphenylphosphino)propane]dichloronickel(II) in tetrahydrofuran (10 niL) stirred at 0 0C. The reaction mixture was stirred at room temperature for 16 hours and the solvent was evaporated under reduced pressure. EtOAc and ammonium chloride in water were added. After extraction, the organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography to yield 1 -cyclopropyl-naphthalene (6.4 g, 76percent).STEP A: 1-CyclopropylnaphthaleneCyclopropylmagnesium bromide (150 mL, 0.5M in tetrahydrofuran) was slowly added to a solution of 1-bromonaphthalene (10 g, 50 mmol) and [l, 3-bis(diphenylphosphino)propane] dichloro nickel (II) in tetrahydrofuran (10 mL) stirred at 0 °C, and the reaction mixture stirred at room temperature for 16 hours. The solvent was removed under reduced pressure and ethyl acetate and aqueous ammonium chloride were added. After extraction, the organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography to yield 1-cyclopropylnaphthalene (6.4 g, 76percent).General procedure: Procedure A: To a Schlenk tube equipped with a magnetic stiring bar and a teflon septum was charged KGeneral procedure: Potassium phosphate (0.75 mmol) and IIe (1 mol percent) was added to the solution of aryl halides (0.25 mmol) and cyclopropylboronic acid (0.5 mmol) in toluene (2.0 mL) and water (100 μL). The mixture was heated to 100 °C for a proper time under nitrogen atmosphere and cooled to room temperature. Water (10 mL) was added and the mixture was extracted with EtOAc (3.x.15 mL), evaporated and purified by chromatography on silica gel.General procedure: 3-dimethylamino-1-(naphthalen-1-yl)propan-1-one hydrochloride (50g, El equivalents) andtriethylene glycol (100 ml) were charged to the reactor at room temperature. 50percent NaOH (E2equivalents) was added while keeping the internal temperature at room temperature. 64percent hydrazine solution in water (E3 equivalents) was added dropwise followed by heating the reaction mixture to a temperature of 80±5°C for a period of 5 hours. Thereafter, water was distilled off in a vacuum of 30-40mbar at a temperature of 80±5°C. The precipitated salt was separated from the reaction mixture by filtration at a temperature of approximately 80°C andsubsequently washed with triethylene glycol brought to a temperature of approximately 80°C (20 Volpercent of the total amount of triethylene glycol).Bringing the reaction mixture to a temperature of 200±10°C for a period of about 5 hours gave crude 1-cyclopropyl-napthalene which was isolated by azeotropic distillation at a temperature of 190±10°C in a vacuum of 30-40mbar. For further purification and isolation ofthe obtained product water was added to the distillate and the product extracted with methyl tert.-butyl ether. The organic phase was washed with water and distilled in a vacuum of 50- lOOmbar at a temperature of 80°C.The isolated pure 1-cyclopropyl-naphtalene was obtained as clear, colorless or pale yellow liquid with a boiling point of 152°C at 13 Torr.In a nitrogen atmosphere, 105 mg of the above nitroaromatic hydrocarbon, 77 mg of the above boric acid compound, 9.2 mg of Pd(acac) 2, 28 mg of imidazolium salt L5, 480 mg of tripotassium phosphate trihydrate, 7.9 were added to the dried sealed tube. Mg 18-crown-6 and 3 mL dioxane, then tighten the capped screw cap and react at 130 C for 48 h. After the reaction, it was filtered through celite, concentrated, and passed through a silica gel column.The product was obtained in 93 mg, yield 93%.Put 500 mL of nitromethane in a dry reaction flask.Ice water is cooled to 0~10 C, Stir, put aluminum chloride(79 g, 592 mmol), stirred for 30 min.1-cyclopropyl naphthalene (50 g, 297 mmol) was charged.Stir for 30 min.Add acetyl chloride (35g, 445.9mmol), Slowly heat up to 0 ~ 10 C and stir for 7 ~ 10h.TLC detection

Molecular Weight:168.23
XLogP3:4.4
Rotatable Bond Count:1
Exact Mass:168.093900383
Monoisotopic Mass:168.093900383
Heavy Atom Count:13
Complexity:181
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes