Dibutyl Vinylboronate (stabilized with Phenothiazine) → 2-Hydroxy-4-vinyl-benzoic acid methyl ester

HRID 1160791Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1160791
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7](I)=[CH:6][C:5]=1[OH:11].[CH2:13](OB(C=C)OCCCC)[CH2:14]CC>C1COCC1.O>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([CH:13]=[CH2:14])=[CH:6][C:5]=1[OH:11]

Komponenten

5

Edukt 2

HCID 236543Dibutyl Vinylboronate (stabilized with Phenothiazine)HCID 11380407Methyl 4-iodosalicylate

Produkt 1

HCID 200893762-Hydroxy-4-vinyl-benzoic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 2-hydroxy-4-iodo-benzoic acid methyl ester (8.01 g, 0.0288 mol) in THF (184 ml) and H2O (46 ml) is treated with vinyl-boronic acid di-butyl ester (9.53 ml, 0.0432 mol, 1.5 eq.), NaCO3 (21.37 g, 0.201 mol, 7 eq.), and dichloro-bis(triphenyl-phosphine)palladium (1.01 g, 1.44 mmol, 5 mol %). The solution is purged with N2 (g) for 5 minutes and then heated to reflux for 2 hour. The reaction is concentrated in vacuo, diluted with EtOAc, and sequentially washed with H2O and saturated aqueous NaCl. The organic phase is dried over MgSO4, filtered, and concentrated. The crude product is purified with silica gel column chromatography (5% ethyl acetate in hexanes) to afford 2-hydroxy-4-vinyl-benzoic acid methyl ester: ESMS m/z 179.1 (M+H+).

Aufarbeitung

  1. customThe solution is purged with N2 (g) for 5 minutes
  2. temperatureheated
  3. temperatureto reflux for 2 hour
  4. concentrationThe reaction is concentrated in vacuo
  5. additiondiluted with EtOAc
  6. washsequentially washed with H2O and saturated aqueous NaCl
  7. dry with materialThe organic phase is dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude product is purified with silica gel column chromatography (5% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-0be8c1c6f39f46659846196c3bd53617
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07816542B2

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