Methyl iodide → HCID 22574235, compound

HRID 1994215Notes

Reaction equation

HRID 1994215 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:18]=[C:19]([F:21])[CH:20]=1)[C:5]([C:10]1[CH:15]=[C:14]([F:16])[CH:13]=[C:12]([F:17])[CH:11]=1)([OH:9])[C:6]([OH:8])=[O:7].[CH2:22]1CCN2C(=NCCC2)CC1.CI>C(#N)C>[F:1][C:2]1[CH:3]=[C:4]([CH:18]=[C:19]([F:21])[CH:20]=1)[C:5]([C:10]1[CH:11]=[C:12]([F:17])[CH:13]=[C:14]([F:16])[CH:15]=1)([OH:9])[C:6]([O:8][CH3:22])=[O:7]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 22574200HCID 22574200, compound

Product 1

HCID 22574235HCID 22574235, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

20.15 g (0.0671 mol) of 3,3′,5,5′-tetrafluorobenzilic acid are placed in 250 ml acetonitrile, 18.6 g (0.121 mol) of DBU, and 34.4 g (0.2426 mol) of methyl iodide is added and then stirred for 6 hours at ambient temperature. The reaction mixture is evaporated to dryness, the residue extracted with ethyl acetate and water, the organic phase dried over MgSO4, evaporated to dryness. The product is recrystallized from cyclohexane. Yield: 15.11 g of beige crystals (68% of theory); melting point: 113° C.-114° C.

Workup

  1. customThe reaction mixture is evaporated to dryness
  2. extractionthe residue extracted with ethyl acetate and water
  3. dry with materialthe organic phase dried over MgSO4
  4. customevaporated to dryness
  5. customThe product is recrystallized from cyclohexane

Sources & evidence

ORD record
ord-89a46e8b07d64150b02e4851d8bf9e16
Source dataset
uspto-grants-2010_01
Patent number
US07652138B2

Reaction notes

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