2-BROMO-4,6-DIFLUOROIODOBENZENE

Step 3. Ethyl 2-(2'-bromo-4', 6'-difluoro-2, 3, 4, 5-tetrahydro-[l, l'-biphenyl]-4-yl)acetate. In a sealed microwave tube, a mixture of ethyl 2-[4-(tetramethyl-l, 3, 2-dioxaborolan-2- yl)cyclohex-3-en-l-yl] acetate (200 mg, 0.68 mmol), [1, 1'- bis(diphenylphosphino)ferrocene]dichloropalladium(II) (24.9 mg, 0.03 mmol), l-bromo-3, 5- difluoro-2-iodobenzene (260 mg, 0.82 mmol) and sodium carbonate (0.85 mL, 2.0 M, 1.7 mmol) in dioxane (3.40 mL) was heated at 70C for 20 h. Upon completion of the reaction, the reaction mixture was filtered through celite, washed thoroughly with EtOAc, and purified via flash chromatography (0-20% EtOAc/heptanes) to obtain the title compound as a colorless oil (210 mg, 86%). 1H NMR (400 MHz, CDCb) d 7.13 (td, /= 2.0, 8.1 Hz, 1H), 6.78 (dt, / = 2.5, 8.8 Hz, 1H), 5.60 (d, / = 1.7 Hz, 1H), 4.17 (q, / = 7.2 Hz, 2H), 2.45 - 2.31 (m, 3H), 2.22 - 2.12 (m, 1H), 2.00 - 1.84 (m, 2H), 1.63 - 1.50 (m, 1H), 1.48 (s, 2H), 1.28 (t, / = 7.1 Hz, 3H). [M+H] = 361.0.Example 133A 2-Bromo-4, 6-difluorobenzaldehyde 1-Bromo-3, 5-difluoro-2-iodobenzene (5.00 g, 15.7 mmol) was dissolved in 2-methyltetrahydrofuran (30 mL) and cooled to 0 C. Isopropylmagnesium chloride lithium chloride complex (1.3 M in tetrahydrofuran, 12.7 mL, 16.5 mmol) was added dropwise. After stirring at 0 C. for 30 min, 4-formylmorpholine (1.99 g, 17.2 mmol) was added. The mixture was warmed to RT and stirred at RT for 4 h. The mixture was quenched with hydrochloric acid (1M in water), diluted with water, and extracted with ethyl acetate. The organic phase was washed with hydrochloric acid (1M in water), water, and brine, and dried over magnesium sulfate. Concentration in vacuo afforded the title compound (2.70 g, 70% of theory) in a purity of 92%. GC-MS (Method 1G): Rt=3.37 min, MS (ESIPos): m/z=219 [M+H]+l-Bromo-3, 5-difluoro-2-iodobenzene (5.00 g, 15.7 mmol) was dissolved in 2-methyltetrahydrofuran (30 mL) and cooled to 0 C. Isopropylmagnesium chloride lithium chloride complex (1.3 M in tetrahydroiuran, 12.7 mL, 16.5 mmol) was added dropwise. After stirring at 0 C for 30 min, 4- formylmorpholine (1.99 g, 17.2 mmol) was added. The mixture was warmed to RT and stirred at RT for 4 h. The mixture was quenched with hydrochloric acid (IM in water), diluted with water, and extracted with ethyl acetate. The organic phase was washed with hydrochloric acid (IM in water), water, and brine, and dried over magnesium sulfate. Concentration in vacuo afforded the title compound (2.70 g, 70% of theory) in a purity of 92%. GC-MS (Method 1G): Rt = 3.37 min, MS (ESIPos): m/z = 219 [M+H]+

Molecular Weight:318.88
XLogP3:3.5
Hydrogen Bond Acceptor Count:2
Exact Mass:317.83527
Monoisotopic Mass:317.83527
Heavy Atom Count:10
Complexity:122
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes