1-(4-(Bromomethyl)phenyl)ethanone

The preparative flow chart is shown in Fig.In a dry round-bottomed flask, 4 ml of p-methyl acetophenone was dissolved in 30 ml of dry acetonitrile, Under the protection of argon, 5.9 g of N-bromosuccinimide (NBS) and 500 mg of azobisisobutyronitrile (AIBN) were added, Continue under the protection of argon 95 ° C reflux 8h, Then cooled to room temperature and the solvent was dried under reduced pressure, The residue was dissolved in 40 ml of methylene chloride, and the organic phase was washed successively with 2M aqueous hydrochloric acid, saturated aqueous sodium hydrogencarbonate and saturated brine, then dried over anhydrous sodium sulfate and the solvent was dried under reduced pressure. The residue was recrystallized from petroleum ether: Ester = 30: 1 (volume ratio) over silica gel column, 6 g of p-bromomethylacetophenone (colorless liquid) was obtained in a yield of 95percent.A mixture of 4-methylacetophenone (2 g, 0.015 mol), Nbromosuccinimide(NBS, 2.66 g, 0.015 mol) and a catalytic amount of benzoyl peroxide in CCl4 wasrefluxed for 4 h. The mixture was hot filtered and evaporated to dryness to afford 22 (2.9 g, 95percent) asbrown oil. 1H-NMR δ 2.51 (s, 3H), 4.52 (s, 2H), 7.40 (d, J = 8.8 Hz, 2H, Ar), 7.91 (d, J = 8.8 Hz, 2H, Ar).P-methylacetophenone (5.4 g, 40 mmol), Sodium bromate (2.4 g, 16 mmol), sodium bromide (3.3 g, 32 mmol)Dichloromethane (25mL) was added to a stirred equipped, Reflux condenser, thermometer and exhaust gas absorption device in the reaction bottle, Heated to reflux and rapidly added 1/3 of the total volume of the initiator solution (0.025 g AIBN, 0.025 g BPO dissolved in 5 mL of dichloromethane), slowlySulfuric acid (2.4 g, 24 mmol concentrated sulfuric acid diluted with 2.5 mL of water) and the remaining initiator solution were subjected to gas chromatography. After completion of the reaction, the mixture was cooled to room temperature and saturated sodium bisulfite solution (10 mL) (10 mL x 2). The organic phases were combined and washed with saturated sodium chloride solution, dried and concentrated. The crude product was purified by column chromatography (10 mL x 2). The organic phase was washed with saturated sodium chloride solution, The elution solvent was ethyl acetate: petroleum ether = 1: 10, volume ratio) to give 8.0 g of p-bromomethylacetophenone in a yield of 94percent. The product was a pale yellow solidp-Methyl-acetophenone (2.0 mL, 14.9 mmol) was dissolved in acetonitrile(10 mL) under nitrogen. N-bromosuccinimide (NBS) (2.92 g, 16.4 mmol) and benzoyl peroxide (BPO) (0.36 g, 1.49 mmol) wereadded and the reaction mixture was stirred for 2 h at 90°C to give a yellow solution. The solvent was removed in vacuo, the residue was dissolved in toluene (20 mL) and filtrated. The filtrate was con-centrated under reduced pressure and purified by silica gel columnchromatography yielded as a white solid (3.0 g, 93percent)Compound MT-026A (5.0 g 37.26 mmol) was dissolved in 200 mL of carbon tetrachloride NBS (2.54 g 44.72 mmol) and benzoyl peroxide (catalytic amount) were added and the reaction was run at reflux for 3 hours under illumination and monitored by TLC. The resulting mixture was filtrated to remove the solid distilled under reduced pressure to remove carbon tetrachloride and purified with a silica gel column chromatography (petroleum ether) to give 7.2 g of the compound MT-026B yield 91. Alternatively the crude product can be obrained without purification for further reaction.Compound MT-026A (5.0 g, 37.26 mmol) was dissolved in 200 mE of carbon tetrachloride, NI3S (2.54 g, 44.72 mmol) and benzoyl peroxide (catalytic amount) were added, and the reaction was run at reflux for 3 hours under illumination and monitored by TEC. The resulting mixture was filtrated to remove the solid, distilled under reduced pressure to remove carbon tetrachloride, and purified with asilica gel column chromatography (petroleum ether) to give 7.2 g of the compound MT-02613, yield: 91percent. Alternatively, the crude product can be obtained without purification forfurther reaction.Intermediate 19 l -(4-(bromomethyl)phenyl)ethanone To a solution ofl-p-tolylethanone (600 mg, 4.47 mmol) in carbon tetrachloride (15 mL) was added N-bromosuccinimide (955 mg, 5.37 mmol) and BPO (31 mg, 0.13 mmol). The mixture was refluxed for 3 h; then it was cooled , and filtered. The filtrate was concentrated to give l -(4- (bromomethyl)phenyl)ethanone (683 mg, 71percent) as a brown oil. LCMS MHTo a solution of 1-p-tolylethanone (600 mg, 4.47 mmol) in carbon tetrachloride 15 mL) was added N-bromosuccinimide (955 mg, 5.37 mmol) and BPO (31 mg, 0.13 mmol). Example 7 EPO MeCN (20ml) solution of 4-methyl acetophenone (2.16g, 15.32mmol) To a stirred solution of, under argon N- bromosuccinimide (3.00g, 16.85mmol) and AIBN (0.25 g, 1.53mmol) was added. The reaction mixture was then heated for 1.5 hours at 90 ° C.. After cooling to room temperature, the solvent was removed under reduced pressure, the residue toluene (25 ml) was added to, and then it was filtered under vacuum. Then the filtrate was concentrated, flash chromatography (10: 1 hexanes / EtOAc, then 5: 1 hexanes / EtOAc) afford the title compound (2.80 g, 86percent) as a colorless oil.

Molecular Weight:213.07
XLogP3:2.3
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:2
Exact Mass:211.98368
Monoisotopic Mass:211.98368
Topological Polar Surface Area:17.1
Heavy Atom Count:11
Complexity:137
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes