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

HRID 928933Notes

Reaction equation

HRID 928933 reaction equation
[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

Participants

11

Reactant 5

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

Product 1

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

Reagents, catalysts & solvents 5

HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolventHCID 12679HexamethylphosphoramideSolventHCID 312751,4-DioxaneSolventHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-Solvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-f8dd96d010bb4bc1b057b85424419897
Source dataset
uspto-grants-2016_03
Patent number
US09290468B2

Reaction notes

Loading…