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CAS No. : | 10485-09-3 | MDL No. : | MFCD06797863 |
Formula : | C9H7Br | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | CCUYEVNCRQDQRF-UHFFFAOYSA-N |
M.W : | 195.06 | Pubchem ID : | 575586 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | With bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; for 24h;Reflux; | 1.2 g (6.2 mmol) of <strong>[10485-09-3]2-bromoindene</strong>, 3.4 g (8.4 mmol) of tributyl-(1H-inden-2-yl)-stannane, 0.44 g (0.63 mmol) of (PPh3)2PdCl2, and 70 mL of THF were refluxed for 24 hours. Then the reaction was added with water and extracted with ethyl acetate for 3 times. The organic layers were combined and dried with anhydrous MgSO4. The solvent was removed by rotary vacuum evaporator and the residue was purified by silica gel chromatography (hexane/dichloromethane = 10/1) to afford 2,2’-biindene (0.79g, 3.4 mmol, 54% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | In hexanes; at -30 - 20℃; for 20.1667h; | In the Glove Box, 32.0 ml of 1.6 M "BuLi (51.2 mmol) in hexanes were added dropwise for 10 min at -3O0C to a solution of 10.0 g (51.3 mmol) of 2- bromoindene in 220 ml of hexanes. This mixture was stirred for 20 h at ambient temperature. The precipitate that formed was filtered off, washed with 3 x 50 ml of hexanes, and dried in vacuum. This procedure gave 7.92 g (77%, 39.4 mmol) of the lithium salt of <strong>[10485-09-3]2-bromoindene</strong>, which was then added at -1000C to a suspension of 4.59 g (19.7 mmol) of ZrCl4 in 200 ml of CH2Cl2. The reaction mixture was slowly warmed for 1 h to 2O0C and, then, stirred for 24 h at ambient temperature. The resulting mixture was filtered through Celite 503 and the filtrate was evaporated to about 70 ml. Crystals that precipitated at -3O0C were separated, washed with 3 x 20 ml of cold hexanes, and dried in vacuum. Yield 11.2 g (52%) of a yellow crystalline product.Anal. calc. for C18H12Br2Cl2Zr: C, 39.29; H, 2.20. Found: C, 39.67; H, 2.39.1H NMR (CD2Cl2): δ 7.46 (dd, J= 6.6 Hz, J= 3.2 Hz, 4H, 4,4',7,7'-H), 7.19 (dd, J= 6.6 Hz, J= 3.2 Hz, 4H, 5,5',6,6'-H), 6.48 (s, 4H, 1,1',3,3'-H).13C NMR (CD2Cl2): δ 128.4, 127.8, 125.9, 110.1, 107.4. |
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