Reaktion #166155

Reaktionsgleichung

potassium carbonate

2-bromophenylboronic acid

2-bromonaphthalene

N2

triphenylphosphine

→

title compound

Ausbeute 79.6%

2-(2-Bromophenyl)naphthalene

Ausbeute 79.6%

Lösungsmittel

1,2-dimethoxyethane

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeTo a 250-mL round bottom flask equipped with a magnetic stir bar
2. 2
   SonstigeThe solution was sparged with nitrogen for 20 minutes
3. 3
   TemperaturAfter cooling to room temperature
4. 4
   Sonstigethe phases were partitioned
5. 5
   Sonstigethe organic layer was collected
6. 6
   WaschenThe aqueous layer was washed with ethyl acetate (3×30 mL)
7. 7
   Waschenthe combined organic fractions were washed with brine (60 mL)
8. 8
   Trocknendried over sodium sulfate
9. 9
   Filtrationfiltered
10. 10
    Einengenconcentrated on a rotary evaporator
11. 11
    SonstigeThe crude orange oil was purified by column chromatography on an Isco CombiFlash system (120-g column

Vorschrift

To a 250-mL round bottom flask equipped with a magnetic stir bar was added water (25 mL) and 1,2-dimethoxyethane (25 mL). The solution was sparged with nitrogen for 20 minutes, and then potassium carbonate (6.67 g, 48.3 mmol, 3 equiv), 2-bromophenylboronic acid (3.80 g, 18.9 mmol, 0.98 equiv) and 2-bromonaphthalene (4.00 g, 19.3 mmol, 1 equiv) were added. The flask was purged with N2 for 10 minutes before finally adding palladium(II) acetate (87 mg, 0.39 mmol, 0.02 equiv) and triphenylphosphine (405 mg, 1.55 mmol, 0.08 equiv). The reaction mixture was heated to 85° C. under a positive pressure of nitrogen for 7 hours. After cooling to room temperature, the phases were partitioned and the organic layer was collected. The aqueous layer was washed with ethyl acetate (3×30 mL), and the combined organic fractions were washed with brine (60 mL), dried over sodium sulfate, filtered, and concentrated on a rotary evaporator. The crude orange oil was purified by column chromatography on an Isco CombiFlash system (120-g column; gradient: 0.5 column volumes heptane, ramp up to 99:1 heptane:dichloromethane over 0.5 column volumes, hold at 99:1 for 1 column volumes, ramp up to 92:8 heptane:dichloromethane over 7 column volumes, hold at 92:8 for 6 column volumes) to afford the title compound as a colorless oil (4.26 g, 97 area % by HPLC, 78% yield). 1H NMR (400 MHz, CDCl3) δ ppm 7.93-7.85 (m, 4H), 7.72 (dd, J=8.0, 1.0 Hz, 1H), 7.57 (dd, J=8.5, 1.7 Hz, 1H), 7.55-7.49 (m, 2H), 7.46-7.38 (m, 2H), 7.28-7.21 (m, 1H).

Quelle