1-Bromo-4-chloro-2-(trifluoromethyl)benzene

Clear colourless to slightly yellow liquid

The diazonium salt solution was prepared as exemplified in example 3. The cold diazonium salt solution was poured into the well stirred and cooled mixture of CuCl (8.9gm., 0.091moles) in concentrated hydrochloric acid (46gm., 0.44moles). The cold mixture is allowed to warm up to room temperature and stirring is continued for 2 to 3 hours. Further heat the reaction mixture to 60 - 70°C to complete the reaction and title compound was isolated. Yield (percent): 65percentThe diazonium salt solution was prepared as exemplified in example 3. The cold diazonium salt solution was poured into the well stirred and cooled mixture of CuCl (8.9gm., 0.091moles) in concentrated hydrochloric acid (46gm., 0.44moles). The cold mixture is allowed to warm up to room temperature and stirring is continued for 2 to 3 hours. Further heat the reaction mixture to 60 - 70°C to complete the reaction and title compound was isolated. Yield (percent): 65percent[0434] To a stirred solution of tert-butyl 2-(((tert-butyldimethylsilyl) oxy) methyl) piperazine-1-carboxylate (3 g, 9 mmol) in toluene (30 mL) under an argon atmosphere were added 1-bromo-4-chloro-2-(trifluoromethyl) benzene (4.7 g, 18 mmol), (±) BINAP (560 mg, 1 mmol), Pd(OAc)2 (203 mg, 1 mmol) and cesium carbonate (8.8 g, 3 mmol) at room temperature and purged under an argon atmosphere for 10 mm. The reaction mixture was stirred at 110 °C for 12 h in a sealed tube. After consumption of starting material (by TLC), the reaction mixture was filtered and the filtrate was concentrated in vacuo. The crude material was purified by column chromatography using 10percent EtOAc/ Hexane to afford tertbutyl 2-((Qert-butyldimethylsilyl) oxy) methyl)-4-(4-chloro-2-(trifluoromethyl) phenyl) piperazine-1-carboxylate (3.7 g, 80percent) as a brown syrup. 'H NMR (DMSO-d 400 MHz): 7.76-7.69 (m, 2H), 7.64 (d, 1H), 4.08 (br s, 1H), 3.91-3.71 (m, 3H), 3.00-2.93 (m, 3H), 2.84 (d, 1H), 2.74-2.66 (m, 1H), 1.42 (s, 9H), 0.85 (s, 9H), 0.05--0.04 (m, 6H); LCMS: 93.0percent; 409 (M-Boc); (column; Ascentis Express C-18 (50 x 3.0 mm, 2.7 jtm); RT 4.42 mm; mobile phase: 0.025percent Aq TFA+5percent ACN: ACN+5percent 0.025percent Aq TFA; T/Bpercent 0.01/5, 0.5/5, 3/100, 5/100: flow rate: 1.2 mL/min) (Gradient); TLC: 50percent EtOAc/ Hexane (Rj: 0.7).A solution of methyl 2-methyl-6-(4, 4, 5, 5-tetramethyl-1, 3, 2-dioxa borolan-2-yl)pyrimidine-4-carboxylate (3) (89 mmol), dioxane and water (2:1) (183 mL) was stirred at room temperature under nitrogen atmosphere. To this reaction mixture, potassium acetate (252 mmol), bis(triphenylphosphine)palladium(II) dichloride (dikis)(35 mmol) and General procedure: A 1, 4-Dioxane solution (8 mL) of 10 (1.0 mmol), arylboronic acid 2 (1.0 equiv.), K3PO4, and Pd(PPh3)4 (5 molpercent) was heated at 75 C for 4 h. After cooling to room temperature, H2O was added and the reaction mixture was extracted with CH2Cl2. The organic layer was dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by column chromatography (pure n-heptane).#10;#10;#10;#10;#10;#10;#10;General procedure: A 1, 4-Dioxane solution (8 mL) of 10 (1.0 mmol), arylboronic acid 2 (1.0 equiv.), K3PO4, and Pd(PPh3)4 (5 molpercent) was heated at 75 C for 4 h. After cooling to room temperature, H2O was added and the reaction mixture was extracted with CH2Cl2. The organic layer was dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by column chromatography (pure n-heptane).#10;#10;#10;#10;#10;#10;#10;General procedure: A 1, 4-Dioxane solution (8 mL) of 10 (1.0 mmol), arylboronic acid 2 (1.0 equiv.), K3PO4, and Pd(PPh3)4 (5 molpercent) was heated at 75 C for 4 h. After cooling to room temperature, H2O was added and the reaction mixture was extracted with CH2Cl2. The organic layer was dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by column chromatography (pure n-heptane).#10;#10;#10;#10;#10;#10;#10;General procedure: A 1, 4-Dioxane solution (8 mL) of 10 (1.0 mmol), arylboronic acid 2 (1.0 equiv.), K3PO4, and Pd(PPh3)4 (5 molpercent) was heated at 75 C for 4 h. After cooling to room temperature, H2O was added and the reaction mixture was extracted with CH2Cl2. The organic layer was dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by column chromatography (pure n-heptane).#10;#10;#10;#10;#10;#10;#10;

Molecular Weight:259.45
XLogP3:3.5
Hydrogen Bond Acceptor Count:3
Exact Mass:257.90587
Monoisotopic Mass:257.90587
Heavy Atom Count:12
Complexity:159
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes