2-Acetyl-6-bromonaphthalene

6-bromo-N-methoxy-N-methyl-2-naphthamide (82.9 g, 282 mmol, 1 equiv.) was dissolved in tetrahydrofurane (600 mL) in a 4-neck flask under nitrogen. The reaction mixture was cooled in an ice bath and methyl magnesium bromide (3.2 M in methyl- tetrahydrofurane, 197 mL, 2.2 equiv.) was added drop wise during 1 hour, while maintaining the temperature of the reaction mixture between 10-15°C. The reaction mixture was stirred 30 minutes further in an ice bath. Aqueous hydrochloric acid (2 M, 100 mL) was then carefully added drop wise while cooling on an ice bath. The organic solvent was evaporated and the precipitated product extracted with dichloromethane (500 mL). The solution was dried over sodium sulphate, filtered and concentrated. The solid residue was dried in vacuum at 40°C yielding l-(6-bromonaphthalen-2-yl)- ethanone (70.6 g, 99 percent).Intermediate 3: l-(6-Bromo-2-naphthalenyl)ethanone (Scheme 1); Methylmagnesium bromide (1.133 mL, 3.40 mmol), was added to 6-bromo-N- methyl-N-(methyloxy)-2-naphthalenecarboxamide (500mg, 1.70 mmol) in THF at 0°C. Stirring continued for 2h at 0°C and allowed to reach T and stirred for additional 12h. Aqueous 0.5 M HCl (ImL) and 0.5mL HAt room temperature, 6-bromo-2-naphthoic acid (AA_072-1, 10 g, 39.83 mmol), N, O-dimethyl hydroxylamine hydrochloride (5.05 g, 51.76 mmol) and DIPEA (15.44 g, 119.49 mmol) were dissolved in DMF (100 mL), HATU (23 g, 59.7 mmol) was added. The reaction mixture was stirred at room temperature for 4 h. After the reaction was complete as detected by TLC, methyl tert-butyl ether (300 mL) was added and the reaction mixture was washed with H2-bromo-naphthalene (0.5 g, 2.41 mmol), AlCl3 (0.338 g, 2.53 mmol) and AcCl (0.172 mL, 2.41 mmol) weredissolved in 3.4 mL of nitrobenzene, and stirred at 100°C for 4 hours under reflux. After addition of water, the reactionsolution extracted with EtOAc. The organic layer was separated, dried with MgSO4 and purified by column chromatographyto obtain the title compound (0.3 g, 49percent).1H-NMR (CDCl3) δ 8.43 (1H, s), 8.06 (2H, m), 7.82 (2H, t), 7.63 (1H, m), 2.72 (3H, s).A mixture of 2-bromonaphthalene (950 g, 4589 mmol), acetyl chloride (260 mL, 4589 mmol), nitrobenzene (6000 mL) and aluminum chloride (642.2 g, 4818 mmol) was stirred for 4 hours at 100°C. The mixture was poured onto ice water, the resulting slurry was filtrated and the organic phase separated from the filtrate. The organic phase was washed with water (2000 mL), dried over NaInto a four-necked flask of 500 ml, Then, 41.4 g of 2-bromonaphthalene, 15.7 g of acetyl chloride, 28 g of aluminum chloride and 250 mℓ of nitrobenzene were charged and stirred at 100 ° C. for 4 hours.Then, upon reaching below cooling to 30 ° C., the reaction mixture was poured into ice water, was removed and the precipitated precipitate was filtered off.The filtrate after washing twice with water 100 ml, dried over anhydrous magnesium sulfate, the solvent was removed under reduced pressure. The residue is recrystallized from hexane to give 18.42g of 2-bromo-6-acetyl naphthalene. (Yield 37.0percent)1H-NMR (400 MHz, CDCl3): δH 2.71 (s, 3H), 7.63 (dd, 1H), 7.80 (d, 1H), 7.82 (d, 2H), 8.05 (M, 2 H), 8.42 (s, 1 H)Alternative for preparation of l-(6-bromonaphthalen-2-yl)ethanone; A mixture of 2-bromonaphthalene (41.4 g, 200 mmol), acetyl chloride (11.3 mL, 160 mmol), nitrobenzene (250 mL) and A1C1To a solution of 2-bromonaphthalene (25 g, 121 mmol) and AlClTo a solution of 2-bromonaphthalene (25 g, 121 mmol) and AICI3 (19.32 g, 145 mmol) in nitrobenzene (227 mL) was added AcCl (10.78 mL, 152 mmol) at 10 °C. The reaction mixture was heated to 40 °C for 18 h. Then the reaction mixture was cooled to rt and poured into ice containing con. HCl (400 mL). The reaction mixture was extracted with EtOAc and washed with 1.5 N HCl solution, brine, dried over NaStep 3

Molecular Weight:249.10
XLogP3:3.5
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:247.98368
Monoisotopic Mass:247.98368
Topological Polar Surface Area:17.1
Heavy Atom Count:14
Complexity:226
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes