Purity | Size | Price | VIP Price | USA Stock *0-1 Day | Global Stock *5-7 Days | Quantity | ||||||
{[ item.p_purity ]} | {[ item.pr_size ]} | Inquiry |
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,1,item.pr_is_large_size_no_price) ]} |
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price) ]} | Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate,item.pr_is_large_size_no_price) ]} | {[ item.pr_usastock ]} | in stock Inquiry - | {[ item.pr_chinastock ]} | {[ item.pr_remark ]} in stock Inquiry - | Login | Inquiry |
Please Login or Create an Account to: See VIP prices and availability
CAS No. : | 24398-88-7 | MDL No. : | MFCD00013529 |
Formula : | C9H9BrO2 | Boiling Point : | - |
Linear Structure Formula : | BrC6H4C(O)OC2H5 | InChI Key : | QAUASTLEZAPQTB-UHFFFAOYSA-N |
M.W : | 229.07 | Pubchem ID : | 90488 |
Synonyms : |
|
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 |
---|---|---|
84% | With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; for 6h;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. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct; caesium fluoride; In 1,2-dimethoxyethane; at 80℃; for 7h;Inert atmosphere; Schlenk technique; | Ethyl 4'-ethoxybiphenyl-3-carboxylate (3) A 20 mL Schlenk tube was dried under vacuum, filled with nitrogen and charged consecutively with 100.0 mg (70 μL, 0.437 mmol, 1.0 eq) ethyl-3-bromobenzoate, 72.5 mg (0.437 mmol, 1.0 eq) 4-ethoxyphenylboronic acid, 139.3 mg (0.917 mmol, 2.1 eq) CsF, 17.8 mg (0.022 mmol, 0.05 eq) PdCl2(dppf)*DCM and 5.0 mL DME. The orange suspension was degassed by vacuum/N2 cycles and stirred at 80 C. for 7 h. GC-MS analysis indicated full conversion (98% product) of the starting material. The reaction mixture was filtered through a pad of celite which was rinsed with EtOAc. The solvent from the filtrate was removed under reduced pressure and final purification by column chromatography (CH/EtOAc 15:1, size: 12.5*2.0 cm, 15 g silica gel) yielded the pure product. yield: 109.5 mg (93%); colorless solid; M.p.: 46-47 C.; Rf (CH/EtOAc 15:1): 0.40; 1H-NMR (300 MHz, CDCl3): δ (ppm)=δ (ppm)=8.25 (t, 4J=1.5 Hz, 1H, Ar-H), 7.98 (d, 3J=7.8 Hz, 1H, Ar-H), 7.74 (d, 3J=7.8 Hz, 1H, Ar-H), 7.56 (d, 3J=9.0 Hz, 2H, Ar-H), 7.48 (t, 3J=7.8 Hz, 1H, Ar-H), 6.98 (d, 3J=9.0 Hz, 2H, Ar-H), 4.41 (q, 3J=7.2 Hz, 2H, CH2), 4.09 (q, 3J=6.9 Hz, 2H, CH2), 1.47-1.39 (m, 6H, 2 CH3); 13C-NMR (75.5 MHz, CDCl3): δ (ppm)=166.6 (C=O), 158.8 (Cq), 141.0 (Cq), 132.5 (Cq), 131.0 (Cq), 130.9 (CHAr), 128.7 (CHAr), 128.2 (2 CHAr), 127.7 (CHAr), 127.6 (CHAr), 114.8 (2 CHAr), 63.8 (CH2), 61.0 (CH2), 14.8 (CH3), 14.3 (CH3); GC-MS (NM-50_S2): tR=7.796 min (m/z=270.1, 99% M+, BP); HRMS (EI+): m/z: calcd for C17H18O3 [M]+: 270.1256; found 270.1260. |
93% | With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct; caesium fluoride; In 1,2-dimethoxyethane; at 80℃; for 7h;Schlenk technique; Inert atmosphere; | General procedure: A Schlenk tube was dried under vacuum, filled with nitrogen and charged consecutively with 1.00 eq bromine substrate, 1.00 eq boronic acid, 2.10 eq CsF, 0.05 eq PdCl2(dppf)*DCM and anhydrous DME (2 mL/0.15 mmol bromoarene). The suspension was degassed by vacuum/N2 cycles and stirred at 80 C. As TLC analysis or GC-MS analysis indicated full conversion of the starting material, the reaction mixture was cooled to rt and filtered through a pad of celite, which was rinsed with EtOAc and/or DCM. The solvent from the filtrate was removed under reduced pressure and final purification by column chromatography or silica gel filtration yielded the pure product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
49% | Under nitrogen, 1,3-dibromobenzene (30.0 g, 127 mmol)Was dissolved in THF (tetrahydrofuran)After dissolving in 300 mL, nBuLi (2.5M) 140 mmol, 56.0 mL was added and stirred at -78 C for 1 hourEthyl-3-bromobenzoate (26.2 g, 114 mmol) is added with a small amount of solvent. After 10 hours, the reaction mixture was slowly warmed to room temperature, quenched with NH4Cl, and extracted with ethyl acetate.The resulting organic solvent layer was dried with anhydrous magnesium sulfate and concentrated under reduced pressure. This was subjected to column chromatography using ethyl acetate: hexane (EA: Hx) to obtain 21.0 g of [intermediate 1-1] (yield = 49%). | |
49% | 1,3-Dibromobenzene (30.0 g, 127 mmol) was dissolved in 300 mL of THF (tetrahydrofuran) under nitrogen, 140 mmol of nBuLi (2.5 M) (56.0 mL) was added and stirred at -78 C for 1 hour. Ethyl 3-Bromobenzoate (26.2 g, 114 mmol) was added with a small amount of solvent. After 10 hours, the temperature was gradually raised to room temperature, and the residue was extracted with NH4Cl and extracted with ethyl acetate (EA). The resulting organic solvent layer was dried with anhydrous magnesium sulfate and concentrated under reduced pressure. This was subjected to column chromatography with EA: Hx to obtain 21.0 g (yield = 49%) of [intermediate 1-1]. |