Sulfuric Acid → 2-Tert-butyl-4-fluorophenol

HRID 423802Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 423802
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[C:9](O)([CH3:12])([CH3:11])[CH3:10].S(=O)(=O)(O)O>C(Cl)Cl>[C:9]([C:6]1[CH:7]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=1[OH:8])([CH3:12])([CH3:11])[CH3:10]

Komponenten

5

Edukt 3

HCID 1118Sulfuric AcidHCID 6386tert-ButanolHCID 97324-Fluorophenol

Produkt 1

HCID 105351102-Tert-butyl-4-fluorophenolAusbeute 42 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

4-Fluorophenol (5 g, 45 mmol) and tert-butanol (5.9 mL, 63 mmol) were dissolved in CH2Cl2 (80 mL) and treated with concentrated sulfuric acid (98%, 3 mL). The mixture was stirred at room temperature overnight. The organic layer was washed with water, neutralized with NaHCO3, dried over MgSO4 and concentrated. The residue was purified by column chromatography (5-15% EtOAc-Hexane) to give 2-tert-butyl-4-fluorophenol (3.12 g, 42%). 1H NMR (400 MHz, DMSO-d6) δ 9.32 (s, 1H), 6.89 (dd,J=11.1, 3.1 Hz, 1H), 6.84-6.79 (m, 1H), 6.74 (dd,J=8.7, 5.3 Hz, 1H), 1.33 (s, 9H).

Aufarbeitung

  1. washThe organic layer was washed with water
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customThe residue was purified by column chromatography (5-15% EtOAc-Hexane)

Quellen und Nachweise

ORD-Eintrag
ord-625747afd8ab40dcb6dddabb003c7b14
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08101767B2

Notizen zur Reaktion

Wird geladen…