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CAS No. : | 108-36-1 | MDL No. : | MFCD00000078 |
Formula : | C6H4Br2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | JSRLURSZEMLAFO-UHFFFAOYSA-N |
M.W : | 235.90 | Pubchem ID : | 7927 |
Synonyms : |
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Signal Word: | Danger | Class: | 9 |
Precautionary Statements: | P280-P302+P352-P305+P351+P338+P310 | UN#: | 3082 |
Hazard Statements: | H315-H318-H335 | Packing Group: | Ⅲ |
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 |
---|---|---|
93% | at 100℃; for 1.5 h; Inert atmosphere | Argon under the protection,A solution of 1,3-dibromobenzene (4.1 g, 17.5 mmol)And AlCl3 (5.6 g, 42 mmol) were placed in a 50 ml two-necked flask,At room temperature,Acetyl chloride (2.0 ml, 28 mmol) was slowly added dropwise,Dripping finished system slowly heated to 100 , a large number of HCl gas release,High temperature reaction for 1.5 hours.System down to room temperature,Slowly pour into crushed ice and concentrated hydrochloric acid.The organic phase was washed with water, washed with Na2CO3 solution and brine, dried over anhydrous MgSO4, and the solvent was evaporated under reduced pressure. The compound 16a (4.5 g, 93percent yield) was isolated by column chromatography. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene at 80℃; for 4.5 h; Sealed tube | Commercial 1,3-dibromobenzene 1 (200.0mg, 0.85mmol), 12 pyrrolidine (60.5mg, 0.85mmol) and 157.0mg of a reagent constituted by 13 tris(dibenzylideneacetone)dipalladium(0), 14 BINAP and 15 t-BuONa (mol ratio: 0.05:0.15:2) were suspended in 16 toluene (2.5mL) and allowed to react in a sealed tube, at 80°C for 4.5h, under magnetic stirring. After cooling to room temperature, the mixture was filtered under reduced pressure and the resulting solution evaporated in vacuo. The residue was dissolved in CHCl3 and washed with a 10percent aqueous solution of 60 NaOH. The organic phase was dried over anhydrous Na2SO4, filtered, evaporated in vacuo, and purified by flash column chromatography on silica gel (petroleum ether), obtaining the intermediate 2 as a transparent oil (190.5mg, 0.84mmol). Yield: 99percent. 1H NMR (CDCl3, 400MHz) δ (ppm): 7.05 (t, 1H, J=8.0Hz), 6.76–6.74 (m, 1H), 6.68 (m, 1H), 6.46 (m, 1H), 3.27–3.24 (m, 4H), 2.05–1.99 (m, 4H). |
54% | With tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene for 4 h; Reflux | 1,3-Dibromobenzene (1.0 g, 4.24 mmol), pyrrolidine (0.43 mL, 5.0 mmol), sodium tert-butoxide (1.14 g, 11.87mmol) and BINAP (0.2 g, 0.32 mmol) were dissolved in 17 mL of toluene. Pd2(dba)3 (0.097 g, 0.1 mmol) was addedthereto, and the mixture was stirred 4 hours under reflux. Solids were filtered through Celite and purified by columnchromatography to obtain the title compound (0.52 g, 54percent).1H-NMR (CDCl3) δ 7.05 (1H, t), 6.75 (1H, d), 6.67 (1H, m), 6.45 (1H, m), 3.26 (4H, m), 2.00 (4H, m) |
45% | With caesium carbonate In toluene at 120℃; | Synthesis of 1-(3-bromophenyl)pyrrolidine Into a 500 mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of 1,3-dibromobenzene (20 g, 84.78 mmol, 1.00 equiv) in toluene (300 mL). To this was added pyrrolidine (6.03 g, 84.80 mmol, 1.00 equiv). Addition of Pd(OAc)2 (190 mg, 0.85 mmol, 0.01 equiv) was next. This was followed by the addition of BINAP (760 mg, 2.53 mmol, 0.03 equiv). To the mixture was added Cs2CO3 (69.1 g, 211.96 mmol, 2.50 equiv). The resulting solution was allowed to react, with stirring, overnight while the temperature was maintained at 120° C. in a bath of oil. The reaction progress was monitored by TLC (EtOAc/PE=1:5). A filtration was performed. The filtrate was concentrated by evaporation under vacuum using a rotary evaporator. The residue was purified by eluding through a column with a PE solvent system. This resulted in 8.51 g (45percent) of 1-(3-bromophenyl)pyrrolidine as a light yellow liquid. LC-MS (ES, m/z): [M+H]+ calcd for C10H13BrN 226, found 226 |
45% | With caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene at 120℃; | Synthesis of 1-3-bromophenyl)pyrrolidine Into a 500 mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of 1,3-dibromobenzene (20 g, 84.78 mmol, 1.00 equiv) in toluene (300 mL). To this was added pyrrolidine (6.03 g, 84.80 mmol, 1.00 equiv). Addition of Pd(OAc)2 (190 mg, 0.85 mmol, 0.01 equiv) was next. This was followed by the addition of BINAP (760 mg, 2.53 mmol, 0.03 equiv). To the mixture was added Cs2CO3 (69.1 g, 211.96 mmol, 2.50 equiv). The resulting solution was allowed to react, with stirring, overnight while the temperature was maintained at 120° C. in a bath of oil. The reaction progress was monitored by TLC (EtOAc/PE=1:5). A filtration was performed. The filtrate was concentrated by evaporation under vacuum using a rotary evaporator. The residue was purified by eluding through a column with a PE solvent system. This resulted in 8.51 g (45percent) of 1-(3-bromophenyl)pyrrolidine as a light yellow liquid. LC-MS (ES, m/z): [M+H]+ calcd for C10H13BrN 226, found 226 |