2-Chloro-4-(Trifluoromethoxy)Bromobenzene

(0.25 g, 0.91 mmol) was added to an flame dried 50 mL round-bottomed flask charged with a stir bar containing tetrahydrofuran (4.0 mL). The solution was placed under Ar2, cooled to -78 C. and n-butyllithium in hexanes (1.1 M, 0.83 mL) was added dropwise. The reaction proceeded for 5 min at -78 C. and then was quickly poured over dry ice. The solvents were evaporated in vacuo and the subsequent oil was partitioned between H2O and hexanes. The aqueous was washed with hexanes (3*10 mL) and then the aqueous was acidified with 1N HCl (10 mL). The product was extracted with EtOAc (3*20 mL), washed with brine (3*10 mL), dried over MgSO4, and concentrated in vacuo. 1H NMR (500 MHz, CDCl3-d) delta ppm 8.11 (d, J=8.7 Hz, 1H) 7.39 (d, J=1.7 Hz, 1H) 7.22 (dd, J=8.8, 1.7 Hz, 1H); HPLC Ret: 6.65 min.To a solution of 1-Bromo-2-Chloro-4-(trifluoromethoxy)benzene (300 mg) in dry THF (1.3 mL) was added isopropylmagnesium chloride lithium chloride complex solution (1.3 M in THF, 1.0 mL) at 0 C. and the resulting mixture was stirred at ambient temperature for 2 h. Trimethyl borate (244 muL) was added at 0 C. and the reaction mixture was stirred at ambient temperature for 1 h. HCl (0.1 M, 1 mL) was added and the mixture was extracted with EtOAc. The combined organic layers were dried and the volatiles were removed under reduced pressure to yield the desired compound (77% yield).To a solution of 1 -Bromo-2-Chloro-4-(trifluoromethoxy)benzene (300 mg) in dry THF (1.3 mL) was added isopropylmagnesium chloride lithium chloride complex solution (1.3 M in THF, 1.0 mL) at 0 C and the resulting mixture was stirred at ambient temperature for 2 h. Trimethyl borate (244 pL) was added at 0 C and the reaction mixture was stirred at ambient temperature for 1 h. HCI (0.1 M, 1 mL) was added and the mixture was extracted with EtOAc. The combined organic layers were dried and the volatiles were removed under reduced pressure to yield the desired compound (77% yield).

Molecular Weight:275.45
XLogP3:4.4
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:1
Exact Mass:273.90079
Monoisotopic Mass:273.90079
Topological Polar Surface Area:9.2
Heavy Atom Count:13
Complexity:176
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes