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CAS No. : | 108-37-2 | MDL No. : | MFCD00000568 |
Formula : | C6H4BrCl | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | JRGGUPZKKTVKOV-UHFFFAOYSA-N |
M.W : | 191.45 | Pubchem ID : | 7928 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H227-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 |
---|---|---|
21% | With caesium carbonate;tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; at 100℃; for 42h; | To 1-(1,1-dimethylethyl) 3-methyl piperazine-1,3-dicarboxylate (1.00g, 4.09 mmol) in dry toluene (15 mL) was added 3-bromo-chlorobenzene (653 mg, 3.41 mmol), Pd2(dba)3 (93.0 mg, 0.102 mmol), BINAP (191 mg, 0.307 mmol), and cesium carbonate (1.11 g, 4.77 mmol). The reaction mixture was stirred at 100 C for 42 h, then cooled to room temperature and filtered through celite. The filter cake was washed with ethanol, and the filtrate was concentrated. Column chromatography on silica (hexanes:ethyl acetate 3: 1) provided 1-(1,1-dimethylethyl) 3-methyl 4-(3-chlorophenyl)piperazine-1,3- dicarboxylate (310 mg, 21% yield) as a colorless oil. 1H NMR (400 MHz, CDC13) 8 7.20- 7.13 (t, 1H), 6.84-6.79 (m, 2H), 6.73-6.78 (d, 1H), 4.63-4.50 (br s, 1H), 4.41-4.32 (br s, 1H), 4.24-4.02 (br s, 2H), 3.71-3.65 (s, 3H), 3.55-3.46 (br s, 1H), 3.42-3.26 (br s, 1H), 3.16-2.97 (br s, 1H), 1.49-1.42 (s, 9H); MS (ESI) for C17H23ClN204: 355 (MH(at)). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With n-butyllithium; In hexane; | EXAMPLE 12 2,3'-Dichloro-2,2-difluoroacetophenone A solution of 25 g of 3-bromochlorobenzene in 100 ml ether was added to a solution of 15.1 g of tetramethylenediamine, 52.4 ml of a 2.5M solution of n-butyllithium in hexane and 75 ml ether at -78 C. under nitrogen. After 1 hour, a solution of 31.0 g of <strong>[383-62-0]ethyl chlorodifluoroacetate</strong> in 150 ml ether was added. After warming to room temperature, the reaction was poured into excess ammonium chloride solution and extracted with ether. The extracts were dried (Na2 SO4) and evaporated. The residue was distilled (0.1 mm Hg) to give 14.7 g of an oil which was used directly. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium carbonate;bis-triphenylphosphine-palladium(II) chloride; In 1,2-dimethoxyethane; water; at 100℃; for 5h; | A mixture of 3,5-di-tert-butylbenzeneboronic acid (175 mg, 0.75 mmole), Bromo-3-chlorobenzene (94 mg, 0.5 mmole), PdCl2(PPh3)2 (10 mg), DME (1.5 mL) and Na2CO3 solution (2N, 0.5 mL) was degassed and stirred at 100° C. for 5 hrs, and allowed to cool down to room temperature, diluted with 5 mL ethyl acetate, dried over sodium sulfate, filtered and concentrated. Column chromatography yield pale yellowish oil as product |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With tris-(dibenzylideneacetone)dipalladium(0); johnphos; sodium t-butanolate; In toluene; for 5h;Inert atmosphere; | General procedure: A round-bottomed flask was charged with Pd2(dba)3 (5 mol percent ), ligand (10 molpercent), aryl halide (1mmol), appropriate isoquinolinamine (1 mmol), base (1.5 mmol) and dry solvent (5 mL). Theflask was flushed with argon for 5 min. The mixture was heated at reflux under magnetic stirring.After cooling down to room temperature, the reaction mixture was concentrated and the residuewas purified by flash column chromatography on silica gel. |