1-Chloro-9H-carbazole synthesis
- Product Name:1-Chloro-9H-carbazole
- CAS Number:5599-70-2
- Molecular formula:C12H8ClN
- Molecular Weight:201.65
Yield:2732-25-4 87.7% ,5599-70-2 8.3%
Reaction Conditions:
with 1,3-di(adamantan-1-yl)-1H-imidazol-3-ium tetrafluoroborate;N-chloro-succinimide;camphor-10-sulfonic acid in 1,4-dioxane at 25; for 24 h;
Steps:
General Procedure A:
General procedure: A mixture of Acetylaniline (0.2 mmol), NCS (0.26 mmol), D-CSA (0.1 mmol) and 1,3-di(1-adamantl)imidazolium tetrafluoroborate (0.01 mmol) in dioxane (1 mL) wasstirred at room temperature (25 oC) under air atmosphere for 24h. The reactionmonitored by GC-MS. When the acetylaniline was consumed completely, the reactionmixture was quenched with saturated aq. NaHCO3 (4 mL). The resulting mixture wasextracted with EtOAc (4 mL x 3). The organic layer was washed with pure water (4ml x 3). The combined organic layer was dried over anhydrous Na2SO4, filtered andthe solvent was removed under reduced pressure to provide the crude product. Thepurification was performed by flash column chromatography on silica gel.
References:
Chen, Jie;Xiong, Xiaoyu;Chen, Zenghua;Huang, Jianhui [Synlett,2015,vol. 26,# 20,art. no. ST-2015-S0670-C,p. 2831 - 2834] Location in patent:supporting information
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