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CAS No. : | 1191028-48-4 | MDL No. : | MFCD22628142 |
Formula : | C8H5BrClN | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | YCQQCNILVIDAPA-UHFFFAOYSA-N |
M.W : | 230.49 | Pubchem ID : | 19918927 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 | UN#: | |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | |
GHS Pictogram: |
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* 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 |
---|---|---|
9.7% | Stage #1: at -40℃; for 1 h; Stage #2: With ammonium chloride In tetrahydrofuran; water at -40 - 20℃; |
A 1.0 M solution of vinylmagnesium bromide in TηF (0.13 L, 130 mmol) is added slowly to 10 g (43 mmol) of 3-bromo-4-chloro-nitrobenzene in 140 mL of TηF at -40 °C. The mixture is stirred at -40 C for an additional hour when aqueous NH4Cl is added. The mixture is allowed to warm to rt, and then is extracted with EtOAc. The extract is washed with brine, dried over MgSO4, filtered, concentrated, and purified twice by chromatography (33percent EtOAc in hexanes) to provide 0.95 g (9.7percent) of 4-bromo-5-chloro-lH-indole and 0.77 g (7.9percent) of 6- bromo-5-chloro-lH-indole. Each of the indole products is separately treated with 1.1 equivalents of BoC2O and 0.2 equivalents of DMAP in MeCN. The mixtures are <n="128"/>concentrated and the residues chromatographed (10percent EtOAc in hexanes) to provide 1-011 (32percent) and 1-012 (48percent). |