Hydroquinone → 4-Bromo-1-fluoro-2-isopropenyl-benzene

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-(5-bromo-2-fluoro-phenyl)-propan-2-ol (119.7 g, 498 mmol) in CH2Cl2 (50 ml) was added hydrochinone (2.74 g, 24.9 mmol) and 250 ml 85% H3PO4. The resulting reaction mixture was stirred for 3.5 h at 50° C. The mixture was poured onto ice-water and extracted with CH2Cl2. The organic phases were washed with 2N aqueous NaOH and water, dried over MgSO4, filtered and concentrated. The crude product was dissolved in hexane and filtered through a plough of silica gel to obtain after concentration at 600 mbar the title compound as a colorless oil: TLC (hexane): Rf=0.52; HPLC RtH5=1.416 min; 1H NMR (360 MHz, CDCl3): δ 7.43 (dd, 1H), 7.37 (m, 1H), 6.94 (dd, 1H), 5.27 (d, 2H), 2.13 (s, 3H).

Provenance & Evidence