Hydrochloric Acid → 2, 3-Difluoro-1-methoxy-4-(4-pentylbicyclo[2.2.2]octyl)benzene

HRID 635144

Reaktionsgleichung

Br[C:2]12[CH2:9][CH2:8][C:5]([CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])([CH2:6][CH2:7]1)[CH2:4][CH2:3]2.[F:15][C:16]1[C:21]([F:22])=[C:20]([O:23][CH3:24])[CH:19]=[CH:18][CH:17]=1.Cl>[N+](C1C=CC=CC=1)([O-])=O.ClCCl.[Fe](Cl)(Cl)Cl>[F:22][C:21]1[C:16]([F:15])=[C:17]([C:2]23[CH2:9][CH2:8][C:5]([CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])([CH2:6][CH2:7]2)[CH2:4][CH2:3]3)[CH:18]=[CH:19][C:20]=1[O:23][CH3:24]

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

A solution of 1-bromo-4-pentylbicyclo[2.2.2]octane (6 g, 23 mmol) in sieve-dried nitrobenzene (100 cm3) is added dropwise to a stirred solution of 2, 3-difluoro-4-methoxybenzene (6 g, 23 mmol) and anhydrous iron(III)chloride (1.2 g, 9 mmol) in sieve-dried nitrobenzene (100 cm3) maintained at 80° C. throughout the addition and overnight. The cooled solution is added to a small volume of hydrochloric acid and stirred for 20 min. The organic layer is separated off and steam-distilled to yield a solid residue. This is taken up in dichloromethane and dried (MgSO4). The raw product is crystallised from ethanol to yield the desired 2, 3-difluoro-1-methoxy-4-(4-pentylbicyclo[2.2.2]octyl)benzene (3.2 g, 44%)

Aufarbeitung

customThe organic layer is separated off
distillationsteam-distilled
customto yield a solid residue
dry with materialdried (MgSO4)
customThe raw product is crystallised from ethanol

Quellen und Nachweise

ORD-Eintrag: ord-ddc99246cd054390a1b76c96b70ac2c5
Quelldatensatz: uspto-grants-2001_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06187393B1

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