2-bromo-5-tert-butylphenol

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

Procedure: Dissolve tetrabutylammonium tribromide (48.1 g, 100 mmol) and 2-tert-butylphenol (15 g, 100 mmol) in CH2Cl2(180 mL) and MeOH (120 mL) at 0° C., and stir overnight. Evaporate the solvent, and partition residue between Et2O (150 mL×3) and water (200 mL). Combine organic layers, and wash with 1M HCl (aqueous, 200 mL) and brine (100 mL), dry over MgSO4, filter, and rotary evaporate to give 23 g (100%) of 2-bromo-5-(1,1-dimethylethyl)phenol as a yellowish oil. 1H NMR (400 MHz, CDCl3) δ 7.39 (d, J=8.5 Hz, 1H), 7.09 (d, J=2.3 Hz, 1H), 6.87 (dd, J=8.5, 2.3 Hz, 1H), 5.57 (s, 1H), 1.31 (s, 9H). 13C NMR (101 MHz, CDCl3) δ 153.15, 151.81, 131.37, 119.22, 113.48, 106.88, 34.68, 31.20. Evaporate the solvent partition residue between Et2O (150 mL×3) and water (200 mL) Combine organic layers, and wash with 1M HCl (aqueous, 200 mL) and brine (100 mL) dry over MgSO4 filter rotary evaporate