Sodium Hydroxide → 6-Bromo-8-chloro-4,4-dimethylchroman

To a mixture of aluminum chloride (403 mg, 3.03 mmol) and dichloromethane (10.0 mL) cooled to −78° C. was added 4-bromo-2-chloro-1-[(3-methylbut-3-en-1-yl)oxy]benzene (758 mg, 2.75 mmol) in dichloromethane (6.00 mL) via a cannula to give a light yellow solution. The reaction mixture was allowed to warm to room temperature, stirred for 5 minutes, and then poured into an Erlenmeyer flask containing a cold 10% NaOH solution (75.0 mL). The mixture was extracted with hexane (40.0 mL, 3×) and the combined organic layers were dried over Na2SO4, filtered, and concentrated under vacuum. The crude mixture was purified by silica gel chromatography eluting with 0-5% EtOAc/hexanes to afford the desired product as a colorless oil.

1. customto give a light yellow solution
2. temperatureto warm to room temperature
3. additionpoured into an Erlenmeyer flask
4. extractionThe mixture was extracted with hexane (40.0 mL, 3×)
5. dry with materialthe combined organic layers were dried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated under vacuum
8. customThe crude mixture was purified by silica gel chromatography
9. washeluting with 0-5% EtOAc/hexanes

ORD record

ord-29283e4f638b4cefa665f3e0720571f6

Source dataset

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08742110B2