3-Chloro-4-iodo-1-(trifluoroMethoxy)benzene

To a mixture of 8-{[tert-butyl(dimethyl)silyl]oxy}-2-azaspiro[4.5]decan-1 -one (500 mg, 1 .76mmol) (isomer 1) and A stirred mixture of 4-(hydroxymethyl)phenylboronic acid (34) (308 mg, 2.03 mmol) and Pd(dppf)Cl2 (191 mg, 0.261 mmol) in toluene (22 mL) and EtOH (11 mL) was degassed for 8 min (vacuum pump) and then N2 was added. An aqueous solution of 2M Na2CO3 (4.4 mL, 8.8 mmol) was added by syringe and the stirred mixture was again degassed for 8 min, and then N2 was added. 2-Chloro-l-iodo-4-(trifluoromethoxy)benzene (35) (585 mg, 1.81 mmol) was added by syringe and the resulting mixture was stirred at 88 0C for 60 min. The cooled mixture was then diluted with aqueous NaHCO3 (100 mL) and extracted with CH2Cl2 (5x 100 mL). The extracts were evaporated to dryness and the residue was chromatographed on silica gel. Elution with 0-50% CH2Cl2/petroleum ether firstly gave foreruns, and then further elution with 50% CH2Cl2/petroleum ether gave 2'-chloro-4'-(trifluoromethoxy)[l, r-biphenyl]-4-yl]methanol (37) (537 mg, 98%) as a white solid: mp (pentane) 38-39 C; 1H NMR (CDCl3) delta 7.46 (br d, J = 8.2 Hz, 2 H), 7.42 (dt, J = 8.3, 2.0 Hz, 2 H), 7.37 (br s, 1 H), 7.36 (d, J = 8.5 Hz, 1 H), 7.19 (m, I H), 4.77 (d, J = 5.9 Hz, 2 H), 1.70 (t, J = 5.9 Hz, 1 H); HREIMS calcd for C14H10ClF3O2 mlz (M+) 304.0292, 302.0321 , found 304.0294, 302.0317.EXAMPLE 2Methods of PreparationA. Synthesis of (6S)-6-[{2'-chloro-4'-(trifluoromethoxy)[1, 1'-biphenyl]-4-yl]methoxy}-2-nitro-6, 7-dihydro-5H-imidazo[2, 1-b][1, 3]oxazine (1) by the method of Scheme 1 A stirred mixture of 4-(hydroxymethyl)phenylboronic acid (34) (308 mg, 2.03 mmol) and Pd(dppf)Cl2 (191 mg, 0.261 mmol) in toluene (22 mL) and EtOH (11 mL) was degassed for 8 min (vacuum pump) and then N2 was added. An aqueous solution of 2M Na2CO3 (4.4 mL, 8.8 mmol) was added by syringe and the stirred mixture was again degassed for 8 min, and then N2 was added. 2-Chloro-1-iodo-4-(trifluoromethoxy)benzene (35) (585 mg, 1.81 mmol) was added by syringe and the resulting mixture was stirred at 88 C. for 60 min. The cooled mixture was then diluted with aqueous NaHCO3 (100 mL) and extracted with CH2Cl2 (5×100 mL). The extracts were evaporated to dryness and the residue was chromatographed on silica gel. Elution with 0-50% CH2Cl2/petroleum ether firstly gave foreruns, and then further elution with 50% CH2Cl2/petroleum ether gave 2'-chloro-4'-(trifluoromethoxy)[1, 1'-biphenyl]-4-yl]methanol (37) (537 mg, 98%) as a white solid: mp (pentane) 38-39 C.; 1H NMR (CDCl3) delta 7.46 (br d, J=8.2 Hz, 2H), 7.42 (dt, J=8.3, 2.0 Hz, 2H), 7.37 (br s, 1H), 7.36 (d, J=8.5 Hz, 1H), 7.19 (m, 1H), 4.77 (d, J=5.9 Hz, 2H), 1.70 (t, J=5.9 Hz, 1H); HREIMS calcd for C14H10ClF3O2 m/z (M+) 304.0292, 302.0321, found 304.0294, 302.0317.

Molecular Weight:322.45
XLogP3:4.4
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:1
Exact Mass:321.88692
Monoisotopic Mass:321.88692
Topological Polar Surface Area:9.2
Heavy Atom Count:13
Complexity:176
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes