Water → HCID 10790583, Verbindung

HRID 325014Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 325014
[Br:1]Br.[CH2:3]([C:10]1[S:14][C:13]2[CH:15]=[CH:16][CH:17]=[CH:18][C:12]=2[C:11]=1[C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=2)=[CH:21][CH:20]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C([O-])(=O)C.[K+].O>C(O)(=O)C>[CH2:3]([C:10]1[S:14][C:13]2[CH:15]=[CH:16][CH:17]=[CH:18][C:12]=2[C:11]=1[C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:26]=[CH:27][C:28]([OH:31])=[C:29]([Br:1])[CH:30]=2)=[CH:21][CH:20]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 24408BromineHCID 517044Potassium AcetateHCID 10548559HCID 10548559, Verbindung

Produkt 1

HCID 10790583HCID 10790583, VerbindungAusbeute 26,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel2×

Versuchsvorschrift

Bromine (1.47 mL, 28.69 mmol) in acetic acid (50 mL) was added dropwise over a 30 minutes period into a cold (5° C.) mixture of 4′-(2-benzyl-benzo[b]thiophen-3-yl)-biphenyl-4-ol (7.5 g, 19.13 mmol), potassium acetate (18.6 g, 190.13 mmol), and acetic acid (200 mL). After the addition the mixture was poured into water, and extracted with ethyl ether. The organic extracts were washed with aqueous sodium bisulfite and dried over MgSO4. Evaporation and purification by flash chromatography on silica gel (hexanes/EtAOc/CH2Cl2 3:1:1) gave 4′-(2-benzyl-benzo[b]thiophen-3-yl)-3-bromo-biphenyl-4-ol as a light yellow solid (2.4 g): mp 54-56° C. MS m/e 477 (M+);

Aufarbeitung

  1. additionAfter the addition the mixture
  2. extractionextracted with ethyl ether
  3. washThe organic extracts were washed with aqueous sodium bisulfite
  4. dry with materialdried over MgSO4
  5. customEvaporation and purification by flash chromatography on silica gel (hexanes/EtAOc/CH2Cl2 3:1:1)

Quellen und Nachweise

ORD-Eintrag
ord-0d01f79f895b4a3397352bcf40521b1c
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06221902B1

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