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

HRID 928938Notes

Reaction equation

HRID 928938 reaction equation
[F:1][C:2]1[C:7]([F:8])=[C:6]([F:9])[CH:5]=[CH:4][C:3]=1[Br:10].S1(CCCC1)(=O)=O.[Li+].CC([N-]C(C)C)C.[Li]CCCC.[C:31](=[O:33])=[O:32]>O1CCOCC1.C(OCC)C.C1COCC1.CN1C(=O)N(C)CCC1.CN(P(N(C)C)(N(C)C)=O)C>[Br:10][C:3]1[C:2]([F:1])=[C:7]([F:8])[C:6]([F:9])=[C:5]([CH:4]=1)[C:31]([OH:33])=[O:32]

Participants

11

Reactant 5

HCID 280Carbon DioxideHCID 31347SulfolaneHCID 2724682Lithium diisopropylamideHCID 27332551-Bromo-2,3,4-trifluorobenzeneHCID 178418339Butyllithium

Product 1

HCID 111186375-Bromo-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 2,3,4-trifluorobromobenzene in appropriate solvent (include 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, nBuLi, LiHDMS) at low temperature (−50-−80° C., prefer −78° C.) under nitrogen atmosphere. The reaction is kept stirring for some time (0.5-12 h, prefer 0.5-2 h) and is added dry ice. After several hours (3-12 h, prefer 5-10 h), 5-bromo-2,3,4-trifluorobenzoic acid is obtained after conventional workup.

Workup

  1. waitAfter several hours (3-12 h, prefer 5-10 h)

Sources & evidence

ORD record
ord-80306c00fd1a499da545dfa8a47cdfe5
Source dataset
uspto-grants-2016_03
Patent number
US09290468B2

Reaction notes

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