Carbon Dioxide → 5-Benzoxy-2,3,4-trifluorobenzoic acid

HRID 928933

Reaktionsgleichung

Reaktionsgleichung von HRID 928933
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([F:15])=[C:11]([F:16])[C:10]=1[F:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S1(CCCC1)(=O)=O.[Li+].CC([N-]C(C)C)C.[Li]CCCC.[C:38](=[O:40])=[O:39]>O1CCOCC1.C(OCC)C.C1COCC1.CN1C(=O)N(C)CCC1.CN(P(N(C)C)(N(C)C)=O)C>[CH2:1]([O:8][C:9]1[C:10]([F:17])=[C:11]([F:16])[C:12]([F:15])=[C:13]([CH:14]=1)[C:38]([OH:40])=[O:39])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

11

Edukt 5

HCID 280Carbon DioxideHCID 31347SulfolaneHCID 2724682Lithium diisopropylamideHCID 833969061-(Benzyloxy)-2,3,4-trifluorobenzeneHCID 178418339Butyllithium

Produkt 1

HCID 897049155-Benzoxy-2,3,4-trifluorobenzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 3283Diethyl EtherLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittelHCID 12679HexamethylphosphoramideLösungsmittelHCID 312751,4-DioxaneLösungsmittelHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-Lösungsmittel

Versuchsvorschrift

To a solution of 1-benzyloxy-2,3,4-trifluorobenzene in appropriate inert solvent (such as, but not limited to, aliphatic and aromatic hydrocarbon (such as pentane, hexane, heptane, cyclohexane, petroleum ether, petrol, gasoline, benzene, toluene, xylene), ether (such as diethyl ether, dibutyl ether, glycol dimethyl ether, 2-methoxyethyl ether, tetrahydrofuran, dioxane), sulfolane, HMPA, DMPU, prefer anhydrous THF, ethyl ether and dioxane) was added strong base (such as LDA, n-BuLi, LiHDMS) at low temperature (−50-−80° C., prefer −78° C.) under nitrogen atmosphere. The stirring was maintained at this temperature for several hours (such as 0.5-12 h, prefer 0.5-2 h). The mixture was transferred to a bottle with dry ice. The mixture is stirred for some time (such as 3-12 h, prefer 5-10 h). 5-Benzoxy-2,3,4-trifluorobenzoic acid is obtained after conventional workup.

Aufarbeitung

  1. temperatureThe stirring was maintained at this temperature for several hours (such as 0.5-12 h, prefer 0.5-2 h)

Quellen und Nachweise

ORD-Eintrag
ord-f8dd96d010bb4bc1b057b85424419897
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09290468B2

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