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N-Formylsaccharin
(CAS RN:50978-45-5 Product Number:F0854)

Structure

N-Formylsaccharin

General Information

Product Number F0854

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Purity/Analysis Method >98.0%(GC)
Storage Temperature
M.F. / M.W. C8H5NO4S=211.19
CAS RN 50978-45-5
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Specification

Purity(GC) min. 98.0 %

References

Reaxys-RN 21741916
PubChem SID 160871419

Application

Easily Accessible and Highly Reactive Crystalline CO Surrogate, N-formylsaccharin

F0854

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 ºC 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

Novel Powerful Formylating Reagent

References

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