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Excepted Quantity | USD 0.00 |
Limited Quantity | USD 15-60 |
Inaccessible (Haz class 6.1), Domestic | USD 80+ |
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CAS No. : | 953408-82-7 | MDL No. : | MFCD11109309 |
Formula : | C8H7ClO3S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 218.66 | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Danger | Class: | 8 |
Precautionary Statements: | P501-P260-P234-P264-P280-P390-P303+P361+P353-P301+P330+P331-P363-P304+P340+P310-P305+P351+P338+P310-P406-P405 | UN#: | 3261 |
Hazard Statements: | H314-H290 | Packing Group: | Ⅱ |
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 |
---|---|---|
94% | In 1,2-dichloro-ethane | 1 Preparation of 7-chlorosulfonyl-2,3-dihydrobenzo[b]furan (2) Example 1 Preparation of 7-chlorosulfonyl-2,3-dihydrobenzo[b]furan (2) 2,3-Dihydrobenzo[b]furan (1) (Aldrich, 5.6 mL, 50 mmol) was added to a suspension of sulfur trioxide-dimethylformamide complex (Aldrich, 9.2 g, 60 mmol) in 1,2-dichloroethane (Aldrich, 20 mL). After being heated at 80° C. for 1 hour, the reaction mixture was cooled to room temperature, and thionyl chloride (Aldrich, 4.5 mL, 57 mmol) was introduced. The reaction mixture was then heated at 70° C. for 3 hours. After cooling down to room temperature, the reaction mixture was poured into ice water (100 mL) which was extracted with ether (3*30 mL). Combined organic layers were washed with brine, then dried (MgSO4). Removal of solvent under vacuum yielded a light yellow solid (10.2 g, 94%). TLC Rf 0.45 (9:1 of hexane-ethyl acetate); MS (electrospray) 219 (M+1); 1H NMR (CDCl3) δ3.35 (t, 2H, J=7.2 Hz), 4.78 (t, 2H, J=7.2 Hz), 6.92 (d, 1H, J=3.1 Hz), 7.82 (s, 1H), 7.83 (d, 1H, J=3.1 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
2. Synthesis of 2,3-dihydrobenzofuran-7-sulfonyl chloride; n-Butyllithium (23 mmol) was added dropwise to a solution of 1,3-dibromo-2-(2-bromoethoxy)benzene (21.8 mmol) in tetrahydrofuran (100 mL) at -100 C. and the reaction mixture was maintained for 30 min. n-Butyllithium (23 mmol) was added dropwise and the reaction mixture was maintained at -100 C. for an additional 60 min. Sulfur dioxide (43.8 mmol) was added and the reaction mixture was maintained for 2 h between -100 and -85 C. The reaction mixture was diluted with hexane (100 mL) and the precipitated solids were collected by filtration. The solid was suspended in dichloromethane (100 mL) at 0 C. and N-chlorosuccinamide (24.6 mmol) was added in several batches. The reaction mixture was maintained for 60 min at 0 C. and was diluted with dichloromethane (100 mL). The reaction mixture was washed with (2 M) sodium hydrogen sulfate (2×150 mL) and brine (3×100 mL), was dried (sodium sulfate), and was concentrated. The residue was purified by Flash chromatography (1/50 ethyl acetate/petroleum ether) to provide 2,3-dihydrobenzofuran-7-sulfonyl chloride in 51% yield as a light yellow solid. Data: 1H NMR: (CDCl3) delta 3.35 (t, 2H), 4.92 (t, 2H), 6.96 (t, 1H), 7.54 (s, 1H), 7.64 (d, 1H). LC/MS (ES) m/z 283 [C13H18N2O3S+H]+. |