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Phenol → Phenylmethyl 4-bromo-2-(phenyloxy)benzoate

HRID 432107
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 432107
[Br:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:7])=[C:4](F)[CH:3]=1.[C:19]1([OH:25])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Br:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:7])=[C:4]([O:25][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:3]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 996PhenolHCID 11430Potassium CarbonateHCID 22351348Benzyl 4-bromo-2-fluorobenzoate

Produkt 1

HCID 22351358Phenylmethyl 4-bromo-2-(phenyloxy)benzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

Phenylmethyl 4-bromo-2-fluorobenzoate (Example 189, 260 mg, 0.84 mmol) was combined with phenol (160 mg, 1.68 mmol, 2.0 eq.) and solid potassium carbonate (580 mg, 4.21 mmol, 5.0 eq.) in anhydrous N,N-dimethylformamide and was heated at 85° C. for 5 hours. The mixture was cooled and partitioned between diethyl ether and water. The aqueous layer was separated and extracted with fresh ether. The organic layers were combined, washed with brine (4×), dried (MgSO4), and concentrated in vacuo to a crude oil. The crude was purified by flash chromatography on silica gel eluted with 95:5 hexanes/ether to provide the title compound as a colorless oil that crystallized upon standing (110 mg, 34%); 1H NMR (300 MHz, CDCl3) δ 7.84 (d, 1H), 7.39-7.27 (m, 7H), 7.17-7.10 (m, 1H), 6.98-6.91 (m, 2H), 6.85 (d, 2H), 5.30 (s, 2H); Rf 0.51 (4:1 hexanes/diethyl ether).

Aufarbeitung

  1. temperatureThe mixture was cooled
  2. custompartitioned between diethyl ether and water
  3. customThe aqueous layer was separated
  4. extractionextracted with fresh ether
  5. washwashed with brine (4×)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo to a crude oil
  8. customThe crude was purified by flash chromatography on silica gel
  9. washeluted with 95:5 hexanes/ether

Quellen und Nachweise

ORD-Eintrag
ord-400375243066421fb70a162f54b95efc
Quelldatensatz
uspto-grants-2003_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06660752B2

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