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CAS No. : | 24410-61-5 | MDL No. : | MFCD15143817 |
Formula : | C8H5FO | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | WPCSQSMSSNPKKB-UHFFFAOYSA-N |
M.W : | 136.12 | Pubchem ID : | 15158726 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | |
Hazard Statements: | H317-H319 | 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 |
---|---|---|
73% | With pyridine; thionyl chloride; at 0℃; for 1.58333h; | Step B: Thionyl chloride (11.0 ml, 150 mmol) was added over a period of 5 minutes to a solution of the product from Step A (2.3 g, 15 mmol) in pyridine (12 ml) at 0 C. and the resulting mixture was stirred at 0 C. for 90 minutes. Dichloromethane (100 ml) was added and the reaction was quenched carefully with 10% aqueous sodium bicarbonate (200 ml) to reach pH 5. Solid sodium bicarbonate (30 g) was then added followed by water (100 ml). The two layers were separated and the aqueous phase was extracted with dichloromethane (100 ml). The combined organic layers were washed with a 5% aqueous sodium bicarbonate (100 ml) and water (100 ml), and were dried over anhydrous magnesium sulfate. The crude was dissolved in dichloromethane and washed with 1N HCl twice and water to remove any residual pyridine. The organic layer was dried over anhydrous magnesium sulfate to give the desired benzofuran (1.5 g, 73%, 98.3% AUC HPLC): 1H NMR (500 MHz, DMSO-d6) delta 7.95 (d, J=1.9 Hz, 1H), 7.36 (d, J=7.6 Hz, 1H), 7.17-7.05 (m, 2H), 6.94 (t, J=2.5 Hz, 1H). |
Compound 1C. 7-Fluorobenzofuran [00114] To a solution of 7-fluoro-2,3-dihydrobenzofuran-3-ol (4.6 g, 29.8 mmol) in pyridine (93 mL) at 0 C was added SOCI2 (21.7 mL, 298 mmol) dropwise. Upon completion of addition, the mixture was stirred at 0 C for 1.5 h. At the conclusion of this period, the reaction mixture was carefully quenched with aqueous aHC03 (saturated, 100 mL) to reach a pH = 9. Once at the prescribed pH, the reaction mixture was extracted with CH2CI2 (4 X 15 mL). The combined organic layers were washed with aqueous NaHCCh (5%, 40 mL), water (40 mL), and then concentrated to yield the crude product. The crude product was dissolved in CH2CI2 (50 mL), washed with aqueous HC1 (1 N, 5 X 10 mL), and then water (40 mL). The organic layer was separated, dried (MgS04), filtered, and concentrated to afford Compound 1C as a brown oil (2.56 g). ? NMR (500 MHz, CDC13) delta ppm 7.67 (d, J=2.2 Hz, 1 H), 7.33 - 7.40 (m, 1 H), 7.17 (td, J=8.0, 4.4 Hz, 1 H), 7.04 (dd, J=10.7, 8.0 Hz, 1 H), 6.79 - 6.85 (m, 1 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
26% | A solution of <strong>[24410-61-5]7-fluorobenzofuran</strong> (0.90 g, 6.6 mmol) in diethyl ether (iO mE) was cooled to 00 C., i.3 mol/L tert-butyllithium (n-pentane solution, 6.i mE, 7.9 mmol) was added dropwise over 20 mi Sulthr dioxide was blown into the reaction mixture for 20 mi N-chlorosuccinimide (i.i g, 9.7 mmol) was added and the mixture was stirred for i hr. The reaction mixture was poured into ice water, extracted with ethyl acetate, and the organic layer was washed with saturated brine, and dried over sodium sulfate. The desiccant was filtered off, the solvent was evaporated and the obtained residue was purified by silica gel column chromatography (petroleum ether) to give the title compound (0.40 g, i.7 mmol, 26%).MS (ESI) mlz 235 (M+H7 | |
Step 1 Preparation of <strong>[24410-61-5]7-fluorobenzo[b]furan</strong>-2-ylsulfonyl chloride. Starting from <strong>[24410-61-5]7-fluorobenzo[b]furan</strong> (10.4 g), the objective compound (5.7 g) was obtained in a manner similar to Step 1 of Example 91. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With bromine; In carbon disulfide; tetrachloromethane; | Step 1 Preparation of 2,3-dibromo-2,3-dihydro-<strong>[24410-61-5]7-fluorobenzo[b]furan</strong>. To a solution of <strong>[24410-61-5]7-fluorobenzo[b]furan</strong> (16 g) in carbon tetrachloride (40 ml) was added dropwise a solution of bromine (22 g) in carbon disulfide (40 ml) at -30 C. and the solution was stirred for 1 hour. At room temperature, the formed precipitate was separated by filtration to give 34.4 g of the objective compound. IR (KBr, cm-1): 1634, 1601, 1489, 1459, 1279, 1179 NMR (CDCl3, ppm): 5.74 (1H, d, J=1.3 Hz), |