1-Bromo-2-methylnaphthalene

CLEAR YELLOW LIQUID

To a stirred CCl4 (20 mL) solution of cyclopentene (2.94 g, 43.1 mmol) were added N-bromosuccinimide (8.06 g, 45.3 mmol)and benzoyl peroxide (catalytic amount). The solution was stirredat reflux for 1 h. The formed solid was removed byfiltration. Thefiltrate was concentrated in vacuo to give 3-bromocyclopentene, which was used to further reaction without purification.To a stirred suspension of NaH (60percent in mineral oil, 2.60 g, 65.0 mmol) in THF (10 mL) was slowly added a THF (5 mL) solutionof malononitrile (5.70 g, 86.2 mmol) at 0 °C under argon atmosphere.The suspension was stirred for 1 h at room temperature. ATHF (5 mL) solution of 3-bromocyclopentene was slowly added at0 °C and the solution was stirred for 2 h at room temperature. Et2Oand brine were added and the organic layer was separated, driedover Na2SO4, filtered, and concentrated in vacuo. The residue wassubjected to silica gel column chromatography (eluent; hexane-AcOEt) to give 3-(dicyanomethyl)cyclopentene (0.889 g, 6.73 mmol, 16percent yield). To a stirred CCl4 (60 mL) solution of 2-methylnaphthalene(20.1 g, 141 mmol), Fe powder (catalytic amount) and I2 (catalyticamount) were slowly added a CCl4 (10 mL) solution of Br2 (22.5 g, 7.2 mL, 141 mmol) at 0 °C. The solution was stirred for 3 h. SatNa2S2O3 aq was added. The organic layer was washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The residuewas subjected to silica gel column chromatography (eluent;hexane) to give 1-bromo-2-methylnaphthalene (29.3 g, 133 mmol, 94percent yield). Brown liquid; 1H NMR (300 MHz, CDCl3) δ 2.58 (s, 3H), 7.26–8.24 (m, 6H) ppm.General procedure: For the typical experiment, to 3 mL of water, anisole (or the other substrate, 5 mmol), NaBr (10 mmol), 1 (2.0 mmol), and 30percent aqueous solution of H1) in 250 ml round-bottom flask to-methylnaphthalene 10.05g2, 12.80g sodium acetate and 30 ml acetic acid solution. In the drip funnel adding 20 ml of acetic acid and 4 ml bromine, the drop in applied to the round-bottom flask, the solution is yellow, to continue stirring 15 minutes, stop reaction. Extraction, drying, concentration, to obtain yellowish oily product (1-bromo-2-methylnaphthalene) 13.7g, yield 87.6percent.A mixed solution of 2-methylnaphthalene (284 mg, 2 mmol), potassium bromide (143 mg, 1.2 mmol), acetic acid 9 ml, water 1 ml, and dichloromethane 5 ml was sequentially charged into a three-necked flask equipped with a condenser and a thermometer, To a constant temperature heated magnetic stirring water bath, slowly added ZnAl-BrO3-LDHs (1.8g, 1.8mmol) in 15min, the reaction temperature was controlled at 40 TCL tracking reaction process, the reaction 5h, washed with sodium sulfite solution , Followed by extraction with methylene chloride (3 x 10 ml). The organic phases were combined and two spatulas of silica gel (200-300 mesh) were added to the dichloromethane phase. The organic solvent was distilled off under reduced pressure and the residue was purified by column chromatography (Petroleum ether: ethyl acetate = 10: 1 as eluent) to give 376 mg of the desired product. Light yellow oily liquid, yield 85percent.

Molecular Weight:221.09
XLogP3:4.2
Exact Mass:219.98876
Monoisotopic Mass:219.98876
Heavy Atom Count:12
Complexity:155
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes