Iodine → 3-(4-Fluorophenyl)propan-1-ol

HRID 5216

Reaktionsgleichung

Reaktionsgleichung von HRID 5216
Br[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][CH:3]=1.[Mg].II.[O:12]1[CH2:15][CH2:14][CH2:13]1.[NH4+].[Cl-]>C1COCC1>[F:8][C:5]1[CH:6]=[CH:7][C:2]([CH2:15][CH2:14][CH2:13][OH:12])=[CH:3][CH:4]=1

Komponenten

7

Edukt 5

HCID 807IodineHCID 99931-Bromo-4-fluorobenzeneHCID 10423OxetaneHCID 25517Ammonium ChlorideHCID 5462224Magnesium

Produkt 1

HCID 137472413-(4-Fluorophenyl)propan-1-olAusbeute 51,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A Grignard reagent was prepared from 4-bromo-1-fluorobenzene (8.0 g)., magnesium turnings (1.10 g), and iodine (one small crystal) in THF (40 ml). Oxetane (2.3 g) in THF (10 ml) was added at RT and the reaction mixture was heated at reflux overnight. The cooled solution was poured into aqueous saturated NH4Cl (100 ml), extracted with ER (2×150 ml) and the combined, dried (Na2SO4) extracts were evaporated. The residual oil was purified by flash chromatography over silica gel (Merck 9285, 0.5 cm wide column), eluting with ER- CX (1:5→1:3). The resultant oil was further purified by distillation to give the title compound (3.15 g) as a colourless oil, b.p. 150°/0.8 torr.

Aufarbeitung

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux overnight
  3. extractionextracted with ER (2×150 ml)
  4. dry with materialdried (Na2SO4) extracts
  5. customwere evaporated
  6. customThe residual oil was purified by flash chromatography over silica gel (Merck 9285, 0.5 cm wide column)
  7. washeluting with ER- CX (1:5→1:3)
  8. distillationThe resultant oil was further purified by distillation

Quellen und Nachweise

ORD-Eintrag
ord-818d644ce64a41d8816409c37119191b
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05243076

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