1-bromo-4-(1-fluoro-2-methylpropan-2-yl)benzene

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

Procedure: 2-(4-Bromophenyl)-2-methylpropan-1-ol (500 mg, 2.182 mmol) was dissolved in Dichloromethane (7.2 mL) in a 20 mL vial. Diethylaminosulfur trifluoride (0.433 mL, 3.27 mmol) was then slowly added To a solution and the resultant mixture was stirred at ambient temperature overnight. At which time, an additional 0.5 eq of DAST was added and stirred for an additional 4 hours. The reaction mixture was purified directly by MPLC on silica gel (eluting with 5% ethyl acetate in hexanes) to afford the title compound. 1H NMR (500 MHz, CDCl3) δ 7.43-7.42 (d, 2H), 7.10-7.09 (d, 2H), 2.88 (s, 1H), 2.83 (s, 1H), 1.35 (s, 3H), 1.30 (s, 3H). The reaction mixture was purified directly by MPLC on silica gel (eluting with 5% ethyl acetate in hexanes)

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

Procedure: 2-(4-bromophenyl)-2-methylpropan-1-ol (500 mg, 2.182 mmol) was dissolved in Dichloromethane (7.2 mL) in a 20 mL vial. DAST (0.433 mL, 3.27 mmol) was then slowly added to the solution. Stirred at ambient temperature overnight. TLC showed presence of starting material. Another 0.5 eq. of DAST was added and stirred for 4 hours. TLC then showed consumption of starting material. The reaction was loaded directly on a silica column and the column was then dried out. Purified with a Teledyne Isco Combiflash Rf purification system using a gradient of 5% EtOAc/hexanes. Isolated 1-bromo-4-(1-fluoro-2-methylpropan-2-yl)benzene as a clear liquid. 1H NMR (500 MHz, CDCl3) δ 7.43-7.42 (d, 2H), 7.10-7.09 (d, 2H), 2.88 (s, 1H), 2.83 (s, 1H), 1.35 (s, 3H), 1.30 (s, 3H). stirred for 4 hours consumption of starting material the column was then dried out Purified with a Teledyne Isco Combiflash Rf purification system

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

Procedure: 2-(4-Bromophenyl)-2-methylpropan-1-ol (500 mg, 2.182 mmol) was dissolved in Dichloromethane (7.2 mL) in a 20 mL vial. Diethylaminosulfur trifluoride (0.433 mL, 3.27 mmol) was then slowly added To a solution and the resultant mixture was stirred at ambient temperature overnight. At which time, an additional 0.5 eq of DAST was added and stirred for an additional 4 hours. The reaction mixture was purified directly by MPLC on silica gel (eluting with 5% ethyl acetate in hexanes) to afford the title compound. 1H NMR (500 MHz, CDCl3) δ 7.43-7.42 (d, 2H), 7.10-7.09 (d, 2H), 2.88 (s, 1H), 2.83 (s, 1H), 1.35 (s, 3H), 1.30 (s, 3H). The reaction mixture was purified directly by MPLC on silica gel (eluting with 5% ethyl acetate in hexanes)