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CAS RN: 50978-45-5 | 產品號碼: F0854
N-Formylsaccharin
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產品規格
| Appearance | White to Almost white powder to crystal |
| Purity(GC) | min. 98.0 % |
性質
| 溶解性（微溶於） | Dimethylformamide |
GHS
相關法規
運輸資料
| HS編碼* | 2925.19-000 |
Application
Easily Accessible and Highly Reactive Crystalline CO Surrogate, N-formylsaccharin
Typical Procedure (entry 1):
Pd(OAc)2 (10.1 mg, 0.045 mmol, 3.0 mol%), DPPB (28.8 mg, 0.068 mmol, 4.5 mol%), N-formylsaccharin (475 mg, 2.25 mmol, 1.5eq.), and Na2CO3 (238 mg, 2.25 mmol, 1.5eq.) are added to a 30 mL test tube, which is then evacuated and backfilled three times with N2. A solution of bromobenzene (158 µL, 1.50 mmol) and Et3SiH (311 µL, 1.95 mmol, 1.3eq.) in DMF (6 mL) is added to the test tube under N2. The tube is immediately sealed and the mixture is stirred efficiently for 10 min at rt. The mixture is subsequently warmed to 75 °C and stirred for a further 16 h. The reaction mixture is cooled to rt, then diluted with Et2O (15 mL), and washed with H2O (15 mL). The aqueous layer is extracted two times with Et2O (15 mL). The combined organic layer is dried over MgSO4, filtered, and concentrated. The obtained residue is purified by flash column chromatography on silica gel (eluent: 3–5% Et2O in n-pentane) to provide benzaldehyde as a colorless oil (132 mg, 83%).
Pd(OAc)2 (10.1 mg, 0.045 mmol, 3.0 mol%), DPPB (28.8 mg, 0.068 mmol, 4.5 mol%), N-formylsaccharin (475 mg, 2.25 mmol, 1.5eq.), and Na2CO3 (238 mg, 2.25 mmol, 1.5eq.) are added to a 30 mL test tube, which is then evacuated and backfilled three times with N2. A solution of bromobenzene (158 µL, 1.50 mmol) and Et3SiH (311 µL, 1.95 mmol, 1.3eq.) in DMF (6 mL) is added to the test tube under N2. The tube is immediately sealed and the mixture is stirred efficiently for 10 min at rt. The mixture is subsequently warmed to 75 °C and stirred for a further 16 h. The reaction mixture is cooled to rt, then diluted with Et2O (15 mL), and washed with H2O (15 mL). The aqueous layer is extracted two times with Et2O (15 mL). The combined organic layer is dried over MgSO4, filtered, and concentrated. The obtained residue is purified by flash column chromatography on silica gel (eluent: 3–5% Et2O in n-pentane) to provide benzaldehyde as a colorless oil (132 mg, 83%).
References
Application
Novel Powerful Formylating Reagent
Reference
- 1)N-Formylsaccharin: A new formylating agent
考研文獻
文檔
產品介紹報導
[TCIMAIL No.158] Novel Powerful N-Formylating Reagent[Product Highlights] Novel Powerful Formylating Reagent
[Research Articles] Easily Accessible and Highly Reactive Crystalline CO Surrogate, N-formylsaccharin
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