Toluene → 1,3-Dibromo-5-isobutoxybenzene

Participants

Reaction Conditions

Reaction Steps

Potassium hydroxide (15.9 g; 284 mmol) was dissolved in water (300 ml) and 3,5-dibromo-phenol (47 g; 188.5 mmol) was added. Benzyl tributylammoniumchloride (17.7 g; 56.8 mmol) and toluene (200 ml) was added and the reaction mixture was heated to 85° C. Bromoethylpropan (32.3 g; 325.7 mmol) was added over 5 hours and the reaction mixture was stirred at 85° C. for additional 16 h. The reaction mixture was cooled to room temperature and the phases were separated. Toluene (100 ml) was added to the organic phase which was washed with 0.2 N aqueous HCl (200 ml×2) and water (200 ml×2). The organic phase was evaporated to give the crude product which was purified by distillation (0.7. mm Hg; Bp: 98° C.); Yield: 43 g (colourless oil).

Provenance & Evidence