Methyl iodide → HCID 67370552, compound

HRID 1678809Notes

Reaction equation

HRID 1678809 reaction equation
[CH2:1]([O:3][C:4](=[O:18])[CH:5]([C:7]1[C:12]([F:13])=[CH:11][C:10]([O:14][CH2:15][CH3:16])=[CH:9][C:8]=1[F:17])[OH:6])[CH3:2].I[CH3:20]>C1(C)C=CC=CC=1.[Ag-]=O>[CH2:1]([O:3][C:4](=[O:18])[CH:5]([C:7]1[C:12]([F:13])=[CH:11][C:10]([O:14][CH2:15][CH3:16])=[CH:9][C:8]=1[F:17])[O:6][CH3:20])[CH3:2]

Participants

5

Reactant 2

HCID 6328Methyl iodideHCID 67372137HCID 67372137, compound

Product 1

HCID 67370552HCID 67370552, compoundYield 97.3%

Reagents, catalysts & solvents 2

HCID 178418778HCID 178418778, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of (4-ethoxy-2,6-difluoro-phenyl)-hydroxy-acetic acid ethyl ester (4.0 g, 15.37 mmol, 1.0 equiv) in toluene (50 mL) was added iodo-methane (21.82 g, 9.78 mL, 153.70 mmol, 10.0 equiv) and silver(I) oxide (7.12 g, 30.74 mmol, 2.0 equiv) and the reaction mixture heated to 60° C. for 18 h. The reaction mixture was filtered, the filtrate poured into ice water and then extracted with ethyl acetate. The organic layer was washed with water, dried over Na2SO4 and concentrated by evaporation under reduced pressure yielding 4.1 g (97%) of the title compound. 1H NMR (300 MHz, CDCl3): 1.25 (t, J=7.5 Hz, 3H), 1.41 (t, J=7.5 Hz, 3H), 3.43 (s, 3H), 4.01 (q, J=7.5 Hz, 2H), 4.26 (q, J=7.5 Hz, 2H), 5.05 (s, 1H), 6.43-6.48 (m, 2H). MS (ISP): 292.3 [M+NH4]+.

Workup

  1. filtrationThe reaction mixture was filtered
  2. additionthe filtrate poured into ice water
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-c89f565790f94f278d2afb605963474b
Source dataset
uspto-grants-2011_08
Patent number
US08008503B2

Reaction notes

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