6-BROMO-TETRAL-1-ON

A solution of NaNO2 (2.35 g, 34 mmol) in water (10 mL) was added dropwise to the solution of 6-amino-1, 2, 3, 4-tetrahydronaphthalen-1-one (5.0 g, 31 mmol) in 25percent HBr (16 mL) at 0°C. The suspension was then transferred to a stirred mixture of CuBr (8.9 g, 62 mmol) in 48percent HBr (30 mL) at 0°C. The resulting mixture was allowed to warm to room temp and stirred for 1 hr. The mixture was extracted with EtOAc, dried (Na2504), and concentrated. The residue was purified by silica gel chromatography (0percent-60percent EtOAc/Hex) to give 5.6 g (80percent) of the title compound as a light yellow oil. ‘H NMR (400 MHz, CDC13): ö 2.10-2.16 (2H, m), 2.64 (2H, t, J=6.4 Hz), 2.94 (2H, t, J=6.0 Hz), 7.42 (1H, s), 7.44 (1H, s), 7.87 (1H, d, J=8.9 Hz). [M+H1 calculated for C, oH9BrO: 225, 227; found: 225, 227.  6-Aminotetralone (47, 500 mg, 3.1 mmol) was dissolved in 25percent HBr (1 mL). The mixture was cooled to 0 °C and a solution of NaNO6-aminotetralone (2.0 g, 12 mmol) was disolved in 25percent HBr (4.0 mL) at 0° C. and then, a solution of NaNOPreparation of Compound 20 , To a stirred solution of XXVI-1 (5.00 g, 0.03 mmol) in 15 mL of 40percent aqueous HBr was added a solution of NaNOReferring to Scheme 2b, to a solution of 2b-l (20.6 g, 0.128 mol) in 45 mL of 48percent hydrobromic acid and 10 mL of water was added a solution of 9.72 g (0.141 mol) of sodium nitrite in 18 mL of water, maintaining a temperature below 5 °C. After stirring at 5 °C for 1 hr, CuBr (0.128 mol) was added and the resulting mixture was stirred at rt for 3 hrs. Subsequently, the mixture was extracted with EtOAc (2 x 200 mL). The extracts were combined, washed with brine, and dried with anhydrous NaReferring to Scheme 12-1, to a solution of 1 (20.60 g, 0.128 mol) in 45 mL of 48percent hydrobromic acid and 10 mL of ]3/4Owas added a solution of 9.72 g (0.141 mol) of sodium nitrite in 18 mL of water, maintaining a temperature below 5 °C. After stirring at 5 °C for 1 h, CuBr (0.128 mol) was added and the resulting mixture was stirred at rt for 3 h. Subsequently, the mixture was extracted with EtOAc (2 x 200 mL). The extracts were combined, washed with brine, and dried with anhydrous Na2S0- Synthesis of compounds of Formula XIVScheme 12-1[0407] Step a. Referring to Scheme 12-1, to a solution of 1 (20.60 g, 0.128 mol) in 45 mL of 48percent hydrobromic acid and 10 mL OfH6-bromo-3, 4-dihydronaphthalen-l(2H)-one. To a solution of 6-amino-3, 4- dihydronaphthalen-l(2H)-one (2.0 g, 12 mmol) in bromic acid (aqueous, 10 mL, 25percent) was added sodium nitrite (0.92 g, 13.3 mmol) at 0°C. The mixture was stirred at 0°C for 15 minutes, and then copper(I) bromide (2.0 g, 13.8 mmol) and bromic acid (aqueous, 20 mL, 25percent) was added at 0°C. After addition completed, the reaction mixture was stirred at room temperature for 1 hour. After the reaction, it was diluted with water (200 mL) and the product was extracted with ethyl acetate (200 mL), dried over anhydrous sodium sulfate, concentrated and purified by column chromatography (silica gel, ethyl acetate/petroleum ether = 1 :20) to give the pure product 6-bromo-3, 4-dihydronaphthalen-l(2H)-one (1.2 g, 45percent). 1H NMR (300 MHz, CDC1To a solution of 6-amino-3, 4-dihydronaphthalen-1(2H)-one (2.0 g, 12 mmol) in bromic acid (aqueous, 10 mL, 25percent) was added sodium nitrite (0.92 g, 13.3 mmol) at 0° C. The mixture was stirred at 0° C. for 15 minutes, and then copper (I) bromide (2.0 g, 13.8 mmol) and bromic acid (aqueous, 20 mL, 25percent) was added at 0° C. After addition completed, the reaction mixture was stirred at room temperature for 1 hour. After the reaction, it was diluted with water (200 mL) and the product was extracted with ethyl acetate (200 mL), dried over anhydrous sodium sulfate, concentrated and purified by column chromatography (silica gel, ethyl acetate/petroleum ether=1:20) to give the pure product 6-bromo-3, 4-dihydronaphthalen-1(2H)-one (1.2 g, 45percent). 6.30. Method ZPreparation of 6-Bromo-3, 4-dihydronaphthalen-1(2H)-one; Under N1-(4-bromophenyl) butanol, 0.4mmolSelectfluor, 0 . 02mmolCu powder, 0.2mmolK

Molecular Weight:225.08
XLogP3:2.7
Hydrogen Bond Acceptor Count:1
Exact Mass:223.98368
Monoisotopic Mass:223.98368
Topological Polar Surface Area:17.1
Heavy Atom Count:12
Complexity:190
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes