Boron trifluoride etherate → HCID 86682286, compound

Temperature

-78 °C

To a 250 mL RBF were added 4-(3-bromo-4-methoxyphenyl)hepta-1,6-dien-4-ol (4.85 g, 16.32 mmol), triethylsilane (5.21 mL, 32.6 mmol), and CH2Cl2 (50 mL). The flask was flushed with N2. BF3.Et2O (2.275 mL, 17.95 mmol) was added via syringe at −78° C. The resulting reaction mixture was stirred at −78° C. for 1 hr and was then allowed to warm to 0° C. briefly. 50 mL 10% KOH was added at 0° C. and the reaction mixture was extracted with 50 mL EtOAc/Hexane (1:1). The organics were washed with 30 mL brine, dried over sodium sulfate, filtered and concentrated. Crude product was purified by silica gel chromatography, eluted with 10% EtOAc/Hexane to give 2-bromo-4-(hepta-1,6-dien-4-yl)-1-methoxybenzene (3.6 g) as colorless oil. 1H NMR (500 MHz, CDCl3:) δ 7.38 (s, 1H), 7.06 (d, 1H), 6.85 (d, 1H), 5.66 (m, 2H), 4.99 (d, 4H), 3.91 (s, 3H), 2.66 (m, 1H), 2.42 (m, 2H), 2.33 (m, 2H).

1. customThe flask was flushed with N2
2. customThe resulting reaction mixture
3. temperatureto warm to 0° C. briefly
4. extractionthe reaction mixture was extracted with 50 mL EtOAc/Hexane (1:1)
5. washThe organics were washed with 30 mL brine
6. dry with materialdried over sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated
9. customCrude product was purified by silica gel chromatography
10. washeluted with 10% EtOAc/Hexane

ORD record

ord-be0e0c610bfa4656b2312970a990b6f6

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09346825B2