Dichloromethane → HCID 10644380, compound

Participants

Reaction Steps

Under nitrogen, 480 mg (0.42 mmol) of Pd(PPh3)4 was added to a stirred solution of 1.64 g (3.93 mmol) of 1,2-dichloro-4-[4-(methylthio)phenyl]-5-(trifluoromethanesulfonyl)benzene (Step 5), 1.1 g (7.9 mmol) of 4-fluorophenylboronic acid and 1.6 g (11.6 mmol) of anhydrous K2CO3 powder in 20 mL of toluene. The reaction was vigorously stirred at reflux for 7 days, and cooled to ambient temperature. The reaction mixture was diluted with ethyl acetate. The resulting solution was washed with water, and dried over MgSO4. Purification by silica gel plug with ethyl acetate/hexane (5:95) gave an oil residue which was subsequently dissolved in 15 mL of CH2Cl2. The resulting solution was treated with 1.4 g (11.8 mmol) of 3-chloroperbenzoic acid (MCPBA) (70%) at 0° C.; and the reaction was stirred overnight at ambient temperature. Excess MCPBA was quenched by the addition of Na2SO3 at 0° C., and stirred for 30 minutes at ambient temperature. The mixture was diluted with CH2Cl2, the resulting solution was washed with water and brine, and dried over Na2SO4. Purification by silica gel chromatography (MPLC) with ethyl acetate/hexane (3:7) gave 505 mg (33%) of 1,2-dichloro-4-(4-fluorophenyl)-5-[4-(methylsulfonyl)phenyl]benzene as a colorless solid: mp 143.5-144.5° C.; NMR (CDCl3) δ 3.05 (s, 3H), 6.95 (d, J=9 Hz, 2H), 6.99-7.07 (m, 2H), 7.30 (d, J=9 Hz, 2H), 7.52 (d, J=9 Hz, 2H), 7.83 (d, J=9 Hz, 2H); MS (CI) m/z 395 (M+H)+; HRMS calc'd for (M+Li)+ 401.0157, found 401.0142. Anal. Calc'd for C19H13O2SFCl2: C, 57.73; H, 3.31; F, 4.81; Cl, 17.94. Found: C, 57.89; H, 3.45; F, 4.81; Cl, 17.56.

Provenance & Evidence