Bromoacetate → HCID 69289771, Verbindung

HRID 347231Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 347231
[H-].[Na+].[Br:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:14]3[CH:15]=[CH:16][C:17]([OH:19])=[CH:18][C:13]=3[S:12][N:11]=2)=[CH:6][CH:5]=1.Br[CH2:21][C:22]([O-:24])=[O:23].OS([O-])(=O)=O.[K+]>C1COCC1>[C:7]([O:24][C:22](=[O:23])[CH2:21][O:19][C:17]1[CH:16]=[CH:15][C:14]2[C:10]([C:7]3[CH:6]=[CH:5][C:4]([Br:3])=[CH:9][CH:8]=3)=[N:11][S:12][C:13]=2[CH:18]=1)([CH3:10])([CH3:8])[CH3:6]

Komponenten

6

Edukt 4

HCID 6226BromoacetateHCID 24758Sodium hydrideHCID 516920Potassium bisulfateHCID 135847952HCID 135847952, Verbindung

Produkt 1

HCID 69289771HCID 69289771, VerbindungAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a suspension of 0.74 g (16.9 mmol) NaH (55% in mineral oil) in 40 ml THF was added a solution of 4 g (13.1 mmol) 3-(4-Bromo-phenyl)-benzo[d]isothiazol-6-ol in 20 ml THF at RT. The solution was stirred at RT for 1 h, 2.1 ml (14.3 mmol) tbutyl bromoacetate was added. The solution was stirred at RT over night, 1M KHSO4 was added carefully and the layers separated. The inorganic one was extracted with EtOAc, the combined organic phases were washed with water and brine and dried over Na2SO4. Column chromatography on silica gel with EtOAc:hexane 1:4 yielded 4.95 g (90%) [3-(4-Bromo-phenyl)-benzo[d]isothiazol-6-yloxy]-acetic acid tert-butyl ester as colorless oil, MS: 420 (MH+,1Br).

Aufarbeitung

  1. stirringThe solution was stirred at RT over night
  2. customthe layers separated
  3. extractionThe inorganic one was extracted with EtOAc
  4. washthe combined organic phases were washed with water and brine
  5. dry with materialdried over Na2SO4

Quellen und Nachweise

ORD-Eintrag
ord-f82690dc2fd04ad8bc1ee22e7c5fbe5a
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07173043B2

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