Methyl iodide → Methyl 3-(3,4-dichlorophenyl)prop-2-enoate

HRID 2294987Notes

Reaction equation

HRID 2294987 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]([OH:13])=[O:12])[CH:5]=[CH:6][C:7]=1[Cl:8].[C:14]([O-])([O-])=O.[Cs+].[Cs+].CI>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]([O:13][CH3:14])=[O:12])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 145483-(3,4-Dichlorophenyl)prop-2-enoic acid

Product 1

HCID 54151376Methyl 3-(3,4-dichlorophenyl)prop-2-enoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Cool a solution of 3-(3,4-dichlorophenyl)-2-propeneoic acid (100 g, 461 mmol) in dry DMF (500 mL) to 0° C. and treat with Cs2CO3 (100 g, 307 mmol). Stir the resulting off-white slurry for 15 min., then add CH3I (33 mL, 530 mmol) via syringe. After 1 h, add additional DMF (250 mL) and stir the slurry for 14 h, then partition between ethyl acetate (EtOAc) (1.5 L) and half saturated aqueous NaHCO3 (500 mL). Separate the organic layer and extract the aqueous layer with EtOAc (1 L, 500 mL). Wash the combined organic layers with half saturated aqueous NaHCO3 (500 mL) and water (5×500 mL), then dry over Na2 SO4 and concentrate to obtain methyl 3-(3,4-dichlorophenyl)-2-propenoate, 105.4 g (456 mmol, 99%, as light brown needles.

Workup

  1. waitAfter 1 h
  2. stirringstir the slurry for 14 h
  3. custompartition between ethyl acetate (EtOAc) (1.5 L) and half saturated aqueous NaHCO3 (500 mL)
  4. customSeparate the organic layer
  5. extractionextract the aqueous layer with EtOAc (1 L, 500 mL)
  6. washWash the combined organic layers with half saturated aqueous NaHCO3 (500 mL) and water (5×500 mL)
  7. customdry over Na2 SO4
  8. concentrationconcentrate

Sources & evidence

ORD record
ord-fc995efec443499dbfa709f43e18c536
Source dataset
uspto-grants-1997_11
Patent number
US05691362

Reaction notes

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