Carbon Dioxide → 2-(tert-Butoxycarbonyl)-6-chloro-4-trifluoromethylbenzoic acid

HRID 3129

Reaktionsgleichung

C(OC(N[C:9]1[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[C:11]([Cl:19])[CH:10]=1)=O)(C)(C)C.[C:20]([Li])([CH3:23])([CH3:22])[CH3:21].[C:25](=[O:27])=[O:26].[OH2:28].[O:29]1[CH2:33]CCC1>CCCCC>[C:20]([O:26][C:25]([C:9]1[CH:14]=[C:13]([C:15]([F:16])([F:17])[F:18])[CH:12]=[C:11]([Cl:19])[C:10]=1[C:33]([OH:29])=[O:28])=[O:27])([CH3:23])([CH3:22])[CH3:21]

Komponenten

Reaktionsbedingungen

Temperatur: -75 °C

Versuchsvorschrift

To a cold (-100° C.) stirred solution of N-(tert-butoxycarbonyl)-3-chloro-5-trifluoromethylaniline 93.4 g, 11.5 mM) in dry tetrahydrofuran (30 mL) under a nitrogen atmosphere was added dropwise t-butyllithium (14.2 mL of 1.7 M solution, 24.2 mM) in pentane. The temperature of the reaction mixture was maintained at -103° to -98° C. during the addition and for 3.25 hr after the addition was completed. Crushed Dry Ice was then added to the cold reaction mixture which, after being allowed to warm to -75° C., was poured into water. The resulting mixture was extracted with ethyl acetate and the combined extracts were dried (MgSO4), filtered and concentrated to leave (3.2 g, 82%) the title compound as a solid white foam.

Aufarbeitung

temperatureThe temperature of the reaction mixture was maintained at -103° to -98° C. during the addition and for 3.25 hr
additionafter the addition
extractionThe resulting mixture was extracted with ethyl acetate
dry with materialthe combined extracts were dried (MgSO4)
filtrationfiltered
concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag: ord-1eb43454a5ef481dbf4ca95331913c1b
Quelldatensatz: uspto-grants-1998_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05733910

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