Ethanol → 1-Bromo-3-isopropoxybenzene

Temperature

78 °C

The following reagents were combined sequentially: anhydrous ethanol (880 ml), potassium carbonate (448.0 g), 3-bromophenol (386.7 g), 2-bromopropane (400.0 g) and finally water (88 ml). The mixture was heated at reflux (78° C.) for 16 hours. Water (880 ml) was added to the reaction mixture and 900 ml of solvent was removed by distillation at atmospheric pressure during a 4 hour period. Heptane (880 ml) was added to the reaction mixture and later separated. The aqueous layer was extracted with heptane (80 ml) and the combined organic fractions were washed sequentially with 1N HCl (300 ml), water (300 ml), 1N NaOH (300 ml) and water (300 ml). Removal of the solvent by rotary evaporation (50° C., 5 mmHg) afforded 453.6 g (97%) of crude product. This was distilled through a short path distillation column (81°-85° C., 2 mmHg) to provide 431.5 g of the product as a colorless liquid.

1. temperatureThe mixture was heated
2. customwas removed by distillation at atmospheric pressure during a 4 hour period
3. additionHeptane (880 ml) was added to the reaction mixture
4. customlater separated
5. extractionThe aqueous layer was extracted with heptane (80 ml)
6. washthe combined organic fractions were washed sequentially with 1N HCl (300 ml), water (300 ml), 1N NaOH (300 ml) and water (300 ml)
7. customRemoval of the solvent
8. customby rotary evaporation (50° C., 5 mmHg)
9. customafforded 453.6 g (97%) of crude product
10. distillationThis was distilled through a short path distillation column (81°-85° C., 2 mmHg)

ORD record

ord-16d25fc307704ba6a20526d0fa153864

Source dataset

uspto-grants-1996_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05498718