Sulfuric Acid → 2-(1-Adamantyl)-4-bromophenol

Participants

Reaction Steps

A 2.0 L three-neck flask attached with a power-stirrer was charged with 4-bromophenol (340.8 g, 1.97 mmol) and 1-adamantanol (300.0 g, 1.97 mmol) in 1.0 L of anhydrous CH2Cl2 at room temperature. Stirring was initiated and once all the reagents were solubilized then concentrated H2SO4 (105 mL, 193.2 g, 1.97 mmol, 1.0 eq) was added dropwise over 15–30 minutes. After approximately 1.0 hour a suspension resulted and the reaction was allowed to continue for a total of 24 hours. The suspension was carefully poured into ice water and neutralized with solid NaHCO3. The resulting layers were separated and the aqueous layer extracted with CH2Cl2 (2×). The combined organics were washed with brine, dried (MgSO4) and filtered. The solvent was removed under reduced pressure and the resulting solid was suspended in a minimal amount of hexanes. After stirring at room temperature for an hour the solid was collected via filtration and dried under reduced pressure to give 495.0 g (77%) of 2-adamantan-1-yl-4-bromophenol as a white solid. 1H NMR (300 MHz; CDCl3): δ 1.77 (s, 6H), 2.08 (s, 9H), 4.81 (s, 1H), 6.53 (d, J=8.4 Hz, 1H), 7.14 (dd, J1=8.7 Hz, J2=2.4 Hz, 1H), 7.29 (d, J=2.4 Hz, 1H).

Provenance & Evidence