2-(4-bromophenyl)-2-methylpropanal

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of 2-(4-bromophenyl)-2-methylpropan-1-ol (10 g, 44 mmol) in dichloromethane (80 mL) was added PCC (14 g, 65 mmol) in portions at 0° C. The resulting solution was stirred at ambient temperature overnight, and then filtered and concentrated in vacuo. The crude residue was purified by flash column chromatography with 1-2% ethyl acetate in hexane to afford the title compound as an off-white solid. 1H NMR (300 MHz, CDCl3) δ 9.49 (s, 1H), 7.52 (d, J=6.3 Hz, 2H), 7.17 (d, J=6.3 Hz, 2H), 1.43 (s, 6H). filtered concentrated in vacuo The crude residue was purified by flash column chromatography with 1-2% ethyl acetate in hexane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of 2-(4-bromophenyl)-2-methylpropan-1-ol (10 g, 44 mmol) in dichloromethane (80 mL) was added PCC (14 g, 65 mmol) in portions at 0° C. The resulting solution was stirred at ambient temperature overnight, and then filtered and concentrated in vacuo. The crude residue was purified by flash column chromatography with 1-2% ethyl acetate in hexane to afford the title compound as an off-white solid. 1H NMR (300 MHz, CDCl3) δ 9.49 (s, 1H), 7.52 (d, J=6.3 Hz, 2H), 7.17 (d, J=6.3 Hz, 2H), 1.43 (s, 6H). filtered concentrated in vacuo The crude residue was purified by flash column chromatography with 1-2% ethyl acetate in hexane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-(4-bromophenyl)-2-methylpropanal (5.7 g, 25 mmol) and trimethyl(trifluoromethyl)silane (7.1 g, 50 mmol) in THF (60 mL) under nitrogen was added a solution of TBAF (0.66 g, 2.5 mmol) in THF (10 mL) dropwise at −30° C. The resulting solution was stirred at −30° C. for 1 hour and at ambient temperature for an additional 1 hour before the addition of 1 N aqueous HCl (20 mL). The mixture was vigorously stirred at ambient temperature for 10 minutes, and then extracted with EtOAc (3×100 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. The crude residue was purified by MPLC on Silica gel (eluting with 2-4% EtOAc/hexane) to afford (S and R)-3-(4-bromophenyl)-1,1,1-trifluoro-3-methylbutan-2-ol as a light yellow oil. The racemic mixture was resolved by preparative chiral HPLC (Chiralpak IA, 2*25 cm; Mobile phase: 5% ethanol in hexane) to afford the two enantiopure title compounds. extracted with EtOAc (3×100 mL) The combined organic layers were dried over sodium sulfate filtered concentrated in vacuo The crude residue was purified by MPLC on Silica gel (eluting with 2-4% EtOAc/hexane)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of 2-(4-bromophenyl)-2-methylpropan-1-ol (10 g, 44 mmol) in dichloromethane (80 mL) was added PCC (14 g, 65 mmol) in portions at 0° C. The resulting solution was stirred at ambient temperature for 16 hours, and then filtered and concentrated in vacuo. The crude residue was purified by MPLC on silica gel (eluting with 1-2% EtOAc/hexane) to afford the title compound as an off-white solid. 1H NMR (300 MHz, CDCl3) δ 9.49 (s, 1H), 7.52 (d, J=6.3 Hz, 2H), 7.17 (d, J=6.3 Hz, 2H), 1.43 (s, 6H). filtered concentrated in vacuo The crude residue was purified by MPLC on silica gel (eluting with 1-2% EtOAc/hexane)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of 2-(4-bromophenyl)-2-methylpropan-1-ol (10 g, 44 mmol) in dichloromethane (80 mL) was added PCC (14 g, 65 mmol) in portions at 0° C. The resulting solution was stirred at ambient temperature overnight, and then filtered and concentrated in vacuo. The crude residue was purified by flash column chromatography with 1-2% ethyl acetate in hexane to afford the title compound as an off-white solid. 1H NMR (300 MHz, CDCl3) δ 9.49 (s, 1H), 7.52 (d, J=6.3 Hz, 2H), 7.17 (d, J=6.3 Hz, 2H), 1.43 (s, 6H). filtered concentrated in vacuo The crude residue was purified by flash column chromatography with 1-2% ethyl acetate in hexane