Sodium Iodide → (5-Tert-butyl-2-methyl-4-thiocyanato-phenoxy)acetic acid methyl ester

HRID 356504Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 356504
[C:1]([C:5]1[C:6]([S:13][C:14]#[N:15])=[CH:7][C:8]([CH3:12])=[C:9]([OH:11])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[Na+].[C:24]([O:27][CH2:28]Br)(=[O:26])[CH3:25]>C(#N)C>[CH3:28][O:27][C:24](=[O:26])[CH2:25][O:11][C:9]1[CH:10]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[C:6]([S:13][C:14]#[N:15])=[CH:7][C:8]=1[CH3:12]

Komponenten

6

Edukt 4

HCID 5238Sodium IodideHCID 10796Cesium carbonateHCID 68536Bromomethyl acetateHCID 105609555-tert-Butyl-2-methyl-4-thiocyanato-phenol

Produkt 1

HCID 54333600(5-Tert-butyl-2-methyl-4-thiocyanato-phenoxy)acetic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a round bottom flask (500 mL) equipped with a magnetic stirrer and condenser were added 2.0 g (9.0 mmol) of 5-tert-butyl-2-methyl-4-thiocyanato-phenol (prepared in Example GGG), cesium carbonate (5.88 g, 18.0 mmol), sodium iodide (4.8 g, 32.0 mmol), and acetonitrile (100 mL). This suspension was heated to reflux for 30 minutes and bromomethyl acetate (1.76 mL, 18.0 mmol) was added via syringe. The reaction was refluxed overnight, cooled to room temperature, quenched with H2O and extracted with EtOAc. The organic layers were combined and dried (MgSO4). The solvent was evaporated and the residue dried under high vacuum to give the title compound. 1H NMR (CDCl3) δ 1.46 (s, 9 H), 2.26 (s, 3 H), 3.82 (s, 3 H), 4.68 (s, 2 H), 6.69 (s, 1 H), 7.52 (s, 1 H),

Aufarbeitung

  1. customTo a round bottom flask (500 mL) equipped with a magnetic stirrer and condenser
  2. temperatureThis suspension was heated
  3. temperatureto reflux for 30 minutes
  4. temperatureThe reaction was refluxed overnight
  5. customquenched with H2O
  6. extractionextracted with EtOAc
  7. dry with materialdried (MgSO4)
  8. customThe solvent was evaporated
  9. customthe residue dried under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-f9cabe04e52a4365970e99a01b6c276b
Quelldatensatz
uspto-grants-1998_11
Patentnummer
US05834506

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