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CAS No. : | 66826-78-6 | MDL No. : | MFCD02677716 |
Formula : | C8H7BrO | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | UDWFSJAYXTXMLM-UHFFFAOYSA-N |
M.W : | 199.04 | Pubchem ID : | 2776159 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | |
Hazard Statements: | H302-H312-H315-H319-H332-H335 | Packing Group: | |
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 |
---|---|---|
With nitrogen; sodium t-butanolate; In toluene; | Example 3 Preparation of N-(2,3-dihydro-1-benzofuran-5-yl)-2,3-dihydro-1-benzofuran-5 -amine To a flask equipped with a magnetic stirrer, reflux condenser, and nitrogen inlet was added <strong>[42933-43-7]2,3-dihydro-1-benzofuran-5-amine</strong> (4.53 grams, 33.3 mmoles, prepared as in Example 23 of U.S. Pat. No. 20040029932), 5-bromo-2,3-dihydrobenzofuran (6.63 grams, 32.9 mmoles), tris(dibenzylideneacetone)dipalladium (0) (0.61 grams, 0.67 mmoles), rac-2,2'-bis(diphenylphosphino)-1,1'-binapthyl (0.83 grams, 1.33 mmoles), sodium tert-butoxide (6.44 grams, 66.6 mmoles) and anhydrous toluene (60 mL). The contents of the flask were refluxed for three days; cooled to room temperature; and filtered through a pad of silica gel. The silica gel pad was then eluted with dichloromethane (200 mL). The combined organic layers were concentrated in vacuo to yield a dark yellow oil. The solid was chromatographed on silica gel, eluding with a hexane/ethyl acetate gradient. The resulting solid was recrystallized from ethanol to afford 1.8 grams of the desired product as a white solid. 1H NMR (CDCl3/D2O) delta 6.55-6.95 (m, 6H), 4.5 (t, 4H), 3.15 (t, 4H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; for 72h;Heating / reflux; | Example 3 Preparation of N-(2,3-dihydro-1-benzofuran-5-yl)-<strong>[42933-43-7]2,3-dihydro-1-benzofuran-5-amine</strong> To a flask equipped with a magnetic stirrer, reflux condensor, and nitrogen inlet was added <strong>[42933-43-7]2,3-dihydro-1-benzofuran-5-amine</strong> (4.53 grams, 33.3 mmoles, prepared as in Example 23 of), 5-bromo-2,3-dihydrobenzofuran (6.63 grams, 32.9 mmoles), tris(dibenzylideneacetone)dipalladium (0) (0.61 grams, 0.67 mmoles), rac-2,2'-bis(diphenylphosphino)-1,1'-binapthyl (0.83 grams, 1.33 mmoles), sodium tert-butoxide (6.44 grams, 66.6 mmoles) and anhydrous toluene (60 mL). The contents of the flask were refluxed for three days; cooled to room temperature; and filtered through a pad of silica gel. The silica gel pad was then eluted with dichloromethane (200 mL). The combined organic layers were concentrated in vacuo to yield a dark yellow oil. The solid was chromatographed on silica gel, eluding with a hexane/ethyl acetate gradient. The resulting solid was recrystallized from ethanol to afford 1.8 grams of the desired product as a white solid. 1H NMR (CDCl3/D2O) delta 6.55-6.95 (m, 6H), 4.5 (t, 4H), 3.15 (t, 4H). |
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