18-Crown-6 → 4-Bromo-2-isopropyl-1-methoxybenzene

Temperature

0 °C

To a suspension of potassium bromide (18.8 g, 157.7 mmol) in 400 mL of CH2Cl2 at 0° C. were added 18-Crown-6 (2.08 g, 7.88 mmol), 3-chloroperoxy benzoic acid (27.2 g, 157.7 mmol) and 2-isopropylanisole (a compound of Formula 1 from Example 1) (12.0 g, 78.8 mmol). After stirring for 3 hours at 0° C., the reaction mixture was poured into ice water (500 mL), and stirred for 30 minutes. The organic layer was separated, washed with saturated NaHCO3 solution (400 mL), followed by water (300 mL), and dried (MgSO4). The solvent was evaporated to give an oil, which was purified by flash column chromatography (silica gel, 98:2 hexane/ethylacetate) to give 13 g (56.7 mmol, 72%) of 4-bromo-2-isopropylanisole (a compound of Formula 3) as an oil; 1HNMR (CDCl3) δ1.2 (d, 6H), 3.3 (heptet, 1H), 6.7 (d, 1H), 6.84 (d, 1H), 7.29 (s, 1H).

1. stirringstirred for 30 minutes
2. customThe organic layer was separated
3. washwashed with saturated NaHCO3 solution (400 mL)
4. dry with materialdried (MgSO4)
5. customThe solvent was evaporated
6. customto give an oil, which
7. customwas purified by flash column chromatography (silica gel, 98:2 hexane/ethylacetate)

ORD record

ord-1ac1ec4cae024a32a755ab183eff0092

Source dataset

uspto-grants-2000_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06107517