Dichloromethane → Ethyl 2-(2-chloro-5-methyl-7-(trifluoromethylsulfonyloxy)benzo[d]thiazol-6-yl)-2-oxoacetate

HRID 879345Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 879345
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.Br[C:24]1[S:25][C:26]2[C:32]([O:33][S:34]([C:37]([F:40])([F:39])[F:38])(=[O:36])=[O:35])=[C:31]([C:41](=[O:47])[C:42]([O:44][CH2:45][CH3:46])=[O:43])[C:30]([CH3:48])=[CH:29][C:27]=2[N:28]=1.C(Cl)[Cl:50]>>[Cl:50][C:24]1[S:25][C:26]2[C:32]([O:33][S:34]([C:37]([F:40])([F:39])[F:38])(=[O:36])=[O:35])=[C:31]([C:41](=[O:47])[C:42]([O:44][CH2:45][CH3:46])=[O:43])[C:30]([CH3:48])=[CH:29][C:27]=2[N:28]=1

Komponenten

4

Edukt 3

HCID 6344DichloromethaneHCID 159087Triacetoxyperiodinane2×HCID 86699782Ethyl 2-(2-bromo-5-methyl-7-(trifluoromethylsulfonyloxy)benzo[d]thiazol-6-yl)-2-oxoacetate

Produkt 1

HCID 86700145Ethyl 2-(2-chloro-5-methyl-7-(trifluoromethylsulfonyloxy)benzo[d]thiazol-6-yl)-2-oxoacetate

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

The above residue was dissolved in CH2Cl2 (33 mL), cooled to 0° C. and Dess-Martin periodinane (2.54 g, 5.99 mmol) was added portion-wise. After stirring for 2 h, more Dess-Martin periodinane (0.25 g, 5.99 mmol) was added. After 1 h, reaction was quenched with Na2S2O3 solution and stirred for 30 minutes. The mixture was diluted with CH2Cl2, washed with water, saturated sodium bicarbonate solution, brine and dried (MgSO4), filtered, concentrated and purified by CombiFlash (0 to 20% EtOAc/Hex) to give product contaminated with ethyl 2-(2-bromo-5-methyl-7-(trifluoromethylsulfonyloxy)benzo[d]thiazol-6-yl)-2-oxoacetate 1H NMR (400 MHz, CDCl3): δ 7.88 (s, 1H), 4.42 (q, J=7.2 Hz, 2H), 2.49 (s, 3H), 1.40 (t, J=7.2 Hz, 3H).

Aufarbeitung

  1. waitAfter 1 h
  2. customreaction
  3. customwas quenched with Na2S2O3 solution
  4. stirringstirred for 30 minutes
  5. additionThe mixture was diluted with CH2Cl2
  6. washwashed with water, saturated sodium bicarbonate solution, brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. custompurified by CombiFlash (0 to 20% EtOAc/Hex)
  11. customto give product

Quellen und Nachweise

ORD-Eintrag
ord-ec671ea85364413588080f6691373f54
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08987250B2

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