Cesium carbonate → Methyl 5-methyl-4-[3-(trifluoromethyl)phenyl]furan-2-carboxylate

HRID 1257437

Reaction equation

HRID 1257437 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]([O:10][CH3:11])=[O:9])[O:5][C:6]=1[CH3:7].[F:12][C:13]([F:24])([F:23])[C:14]1[CH:15]=[C:16](B(O)O)[CH:17]=[CH:18][CH:19]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:7][C:6]1[O:5][C:4]([C:8]([O:10][CH3:11])=[O:9])=[CH:3][C:2]=1[C:18]1[CH:17]=[CH:16][CH:15]=[C:14]([C:13]([F:24])([F:23])[F:12])[CH:19]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 604544Methyl 4-bromo-5-methylfuran-2-carboxylateHCID 27343883-(Trifluoromethyl)phenylboronic acid

Product 1

HCID 66939668Methyl 5-methyl-4-[3-(trifluoromethyl)phenyl]furan-2-carboxylateYield 61.6%

Reagents, catalysts & solvents 1

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Catalyst

Procedure

By a method similar to that in Example 126c and using the compound (1.00 g) obtained in Example 128b, 3-(trifluoromethyl)phenylboronic acid (1.04 g), cesium carbonate (2.98 g, 3.6 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.19 g), the title compound (0.80 g) was obtained as a solid.

Sources & evidence

ORD record
ord-1f74dbfc745b413db299c206ace20811
Source dataset
uspto-grants-2013_06
Patent number
US08461348B2

Linked notes

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