Ethanone, 2-broMo-1-(3,5-dichlorophenyl)- (Related Reference)

i) General procedure: Thiocarbamate 5 (1 mmol) and 2-bromo-1-phenylethanone 6a-w (1.1 mmol) were dissolved in ethanol (10 mL) and refluxed for 3-5 h (monitored by TLC). After cooling to room temperature, the solvent was evaporated under reduced pressure, aqueous sodium hydroxide solution (10 mL of a 1.0 M solution) was added and the mixture was extracted with dichloromethane (310 mL). The combined organic layers were dried over anhydrous MgSO4, filtered, and concentrated in vacuo. The residue was purified by flash silica-gel column chromatography (DCM/MeOH 10:1, v/v).General procedure: Ammonium dithiocarbamate (2 mmol) was dissolved in a mixture of ethanol (2 mL) and water (2 mL). 2-bromo-1-phenylethanone 6a-w (1 mmol) in ethanol (2 mL) was added dropwise at 0 C and the mixture was refluxed for 3-5h. The organic solvent was evaporated under reduced pressure and extracted with ethyl acetate (310 mL). The combined organic layers were dried over anhydrous MgSO4, filtered, and concentrated in vacuo.To a stirred solution of 5-bromo-N?-hydroxy-6- methoxypicolinimidamide (500 mg, 2 mmol) in DMF (10 mL) at room temperature under an argon atmosphere were added potassium carbonate (560 mg, 4 mmol) and 2-bromo-1-(3, 5- dichlorophenyl) ethan-1-one (817 mg, 3 mmol). The reaction mixture was stirred for 30 mm at 80 C in microwave. After consumption of starting material (monitored by TLC), the reaction mixture was diluted with water (20 mL) and extracted with EtOAc (2 x 20 mL). The combined organic extracts were dried over sodium sulfate, filtered and concentrated in vacuo to afford (Z)-5-bromo-iV-(2-(3 , 5-dichlorophenyl)-2-oxoethoxy)-6-methoxypicolinimidamide (600 mg, crude) as brown semi solid used in the next step without further purification.[0674] LCMS: 30.8%; 433.6 (M+3); (column; Ascentis Express C-18 (50 x 3.0 mm, 2.7 pm); RT 2.88 mm; mobile phase: 0.025% Aq TFA+5% ACN: ACN+5% 0.025% Aq TFA; T/B%: 0.01/5, 0.5/5, 3/100, 5/100; flow rate: 1.2 mL/min) (Gradient); TLC: 30% EtOAc/ Hexane (R1 0.6).0.14g (1mmol) tropinone, 0.091g (1mmol) thiosemicarbazide and 0.26g (1mmol) of crude product alpha- bromo-4- (3, 5-dichloro) acetophenone was dissolved in 2mL of ethanol, microwave 100 deg.C, the reaction 10min, TLC tracking, completion of the reaction, the solvent was removed under reduced pressure, the reaction mixture was 30mL of deionized water, (3 × 20mL) and extracted with dichloromethane and the combined organic phase was dried over anhydrous magnesium sulfate, and removed under reduced pressure The solvent system was purified by flash column to give the title compound in 70% yieldThe intermediate 3, 5-dichlorostyrene oxide needed for preparing the title compound is made by reducing 28.4 g of The intermediate 3, 5-dichlorostyrene oxide needed for preparing the title compound is made by reducing 28.4 g of

Molecular Weight:267.93
XLogP3:3.7
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:2
Exact Mass:265.89008
Monoisotopic Mass:265.89008
Topological Polar Surface Area:17.1
Heavy Atom Count:12
Complexity:164
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes