Nitrogen → 3-(4-Fluoro-2-methylsulfanyl-phenyl)-acrylic acid methyl ester

HRID 1971845Notes

Reaction equation

HRID 1971845 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5](I)=[C:4]([S:9][CH3:10])[CH:3]=1.C([O-])([O-])=O.[K+].[K+].[C:17]([O:21][CH3:22])(=[O:20])[CH:18]=[CH2:19].N#N>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2].O>[CH3:22][O:21][C:17](=[O:20])[CH:18]=[CH:19][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][C:4]=1[S:9][CH3:10]

Participants

9

Reactant 4

HCID 947NitrogenHCID 7294Methyl AcrylateHCID 11430Potassium CarbonateHCID 58127007(5-Fluoro-2-iodophenyl)(methyl)sulfane

Product 1

HCID 669225163-(4-Fluoro-2-methylsulfanyl-phenyl)-acrylic acid methyl esterYield 89%

Reagents, catalysts & solvents 4

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

4-fluoro-1-iodo-2-methylsulfanyl-benzene (6.8 g 25.3 mmol), K2CO3 (9.9 g, 63.4 mmol), methyl acrylate (5.7 ml, 63.4 mmol), Tetra-n-butylammonium chloride (7.0 g, 25.3 mmol) and Pd(OAc)2 (1.1 g, 5.07 mmol) were mixed in DMF (150 ml). The mixture was heated at 50° C. under the atmosphere of N2 overnight, after which water was added and then extracted with ethyl acetate. The extracts were combined, washed with brine, dried over sodium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography to give the desired product (4.8 g, yield 89%).

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. customevaporated under reduced pressure
  5. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-a58fd78498504445a13fd200f17eda87
Source dataset
uspto-grants-2013_04
Patent number
US08431581B2

Reaction notes

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