Potassium Hydroxide → 2,7-Dichloro-9-(3,7-dimethyl-octyl)-9H-carbazole

Temperature

85 °C

2,7-Dichlorocarbazole (synthesized according to the procedure by Leclerc et al: Morin, Jean-Francois; Leclerc, Mario; Macromolecules (2001), 34(14), 4680–4682) (10.7 g, 45.3 mmol) was added to a 50% w/w aqueous solution of potassium hydroxide (75 ml) and Aliquat-336 (0.5 ml). 1-Bromo-3,7-dimethyloctane (12.0 g, 54.3 mmol) was added dropwise and the reaction mixture was heated at 85° C. for 12 h. After cooling to room temperature, methylene chloride was added. The reaction mixture was transferred to a separation funnel and the organic layer was removed. The aqueous layer was extracted with methylene chloride (3×) and the combined organic layers were dried over magnesium sulfate. After removal of the solvent in vacuo, the crude product was purified by column chromatography (silica gel, hexane) to yield 13.5 g of the product as colorless solid.

1. temperatureAfter cooling to room temperature
2. customThe reaction mixture was transferred to a separation funnel
3. customthe organic layer was removed
4. extractionThe aqueous layer was extracted with methylene chloride (3×)
5. dry with materialthe combined organic layers were dried over magnesium sulfate
6. customAfter removal of the solvent in vacuo
7. customthe crude product was purified by column chromatography (silica gel, hexane)

ORD record

ord-0712d418553b47908225e48228690562

Source dataset

uspto-grants-2006_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07138483B2