1-Bromo-4-methylnaphthalene

General procedure: A mixture of 1-methylnaphthalene (14, 28.44 g, 200 mmol) and NBS (39.16 g, 220 mmol) inMeCN (300 mL) was stirred at 30-40°C until completion of the reaction as indicated by TLC analysis(typically within 12 h). On cooling to room temperature, the reaction mixture was poured intoice-water (600 mL), and the resulting mixture was extracted with CH2Cl2 (500 mL × 3). The combinedextracts were washed successively with 5percent aqueous Na2S2O3 (200 mL), saturated aqueous Na2CO3(100 mL × 3) and 5percent brine (200 mL), dried (Na2SO4) and evaporated on a rotary evaporator to give aresidue, which was purified by column chromatography to afford 1-bromo-4-methylnaphthalene(15). Colorless oil, 42.01 g (98percent). 1H-NMR (DMSO-d6, 400 MHz) δ: 8.14–8.16 (m, 1H), 8.07–8.09 (m, 1H), 7.76 (d, J = 7.6 Hz, 1H), 7.66–7.70 (m, 2H), 7.30 (d, J = 7.6 Hz, 1H), 2.63 (s, 3H).General procedure: To a stirred solution of 1-(cyclo)alkylnaphthalene (2a-2e, 0.13 mol) in MeCN (200 mL) at room temperature was added NBS (24.92 g, 0.14 mol), and the resulting mixture was stirred at 30-40°C until completion of the reaction as indicated by TLC analysis (typically within 24 h). On cooling to room temperature, the reaction mixture was poured into ice-water (800 mL), and the resulting mixture was extracted with CH1-Methylnaphthalene (3.0 g, 21 mmol, 1.0 eq)And N-bromosuccinimide (4.1 g, 23 mmol, 1.1 eq) were added to 60 mL of dimethylsulfoxide and heated at 90 ° C for 10 hours. After completion of the TLC reaction of the starting material, the reaction was stopped. Add 60mL of purified water, 3 * 40mL ethyl acetate extraction, combine the organic layer, with 40mL saturated sodium chloride water, anhydrous magnesium sulfate, concentrated to half volume, placed in ice water bath stirring crystallization, Bromo-1-Methylnaphthalene solid4.05 g, Yield 88.37percent.The compounded 4' (10 mmol, 2.21 g) was added to a mixture of 30 ml of ether and 30 ml of benzene, and n-butyllithium (10 mmol, 1.6 M, 6.25 ml) was slowly added dropwise at 0°C under nitrogen atmosphere. After stirring at 0° C. for 1 hour, methyl iodide (15 mmol, 2.13 g) was slowly added dropwise to the reaction system. After completion of the dropwise addition, the reaction was warmed up to room temperature. The reaction was completed by TLC and the reaction was completed. 60 ml of a saturated aqueous solution of ammonium chloride was added to the reaction system, the aqueous layer was extracted with toluene, the organic layers were combined, washed with saturated brine (100ml*3), dried over anhydrous sodium sulfate, and the organic phase was concentrated and purified by column chromatography. Compound 4''' (7.3 mmol, 1.61 g, 73percent).

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