1-(4-Bromo-2-chlorophenyl)ethanone

Step 6-J: 4-BROMO-2-CHLORO-THIOBENZOIC acid S-PYRIDIN-2-YL ester (1.86 g, 5.66 mmol) from Step 1 above was dissolved in dry THF (30 mL) and cooled to-78 C. A solution of methyl magnesium bromide in 75: 25 toluene/THF (1.4 M, 4.45 mL, 6.23 mmol) was added dropwise. After stirring 35 min, the cooling bath was removed. The reaction mixture was quenched with saturated 1 N HCI and extracted with EtOAc (30 mL). The organic phase was washed with brine (50 mL), dried over NA2SO4 and evaporated. The residue was purified by flash column chromatography (10percent EtOAc in hexanes) to give the product (1.05 g, 80percent) as a colorless oil. 1H NMR (CDC13) 8 2.64 (s, 3H), 7.46-7. 48 (m, 2H), 7.61 (s, 1H).4-Bromo-2-chloro-thiobenzoic acid S-pyridin-2-yl ester (1.86 g, 5.66 mmol) from Step 1 above was dissolved in dry THF (30 mL) and cooled to -78° C. A solution of methyl magnesium bromide in 75:25 toluene/THF (1.4 M, 4.45 mL, 6.23 mmol) was added dropwise. After stirring 35 min, the cooling bath was removed. The reaction mixture was quenched with saturated 1N HCl and extracted with EtOAc (30 mL). The organic phase was washed with brine (50 mL), dried over NaTo a solution of 4-bromo-2-chloro-N-methoxy-N-methylbenzamide (13.3 g, 47.76 mmol) in tetrahydrofurane (100 mL) was added methylmagnesiumbromide (71.63 mmol) at -60°C under nitrogen. The reaction mixture was stirred at -60 °C for 1 hour, then stirred at 25 °C for 3 hours. A saturated aqueous solution of ammonium chloride was added. The reaction mixture was extracted with ethylacetate (100 mL) twice. The organic layer was washed by brine, dried with sodium sulfate and concentrated in vacuo. This afforded the title compound (9.7 g) as brown solid. LCMS (M+H)(2) 1- (4-bromo-2-chlorophenyl) ethanol (270mg)Of chloroform (5mL)Solution to manganese dioxide (1.0g)It was added, and the mixture was stirred for 3 hours at an external temperature of 40 .The reaction mixture was diluted with chloroform and another Delo Celite (registered trademark), and the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane: ethyl acetate = 95: 5 → 70: 30), to thereby yield 1- (4-bromo-2-chlorophenyl) ethanone (100 mg) as a colorless oily substance.

Molecular Weight:233.49
XLogP3:2.9
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:231.92906
Monoisotopic Mass:231.92906
Topological Polar Surface Area:17.1
Heavy Atom Count:11
Complexity:160
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes