Chlorodifluoromethane → HCID 22625606, compound

HRID 277668Notes

Reaction equation

HRID 277668 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]=[C:11]([CH3:14])[NH:12][CH:13]=1.Cl[CH:16]([F:18])[F:17]>O1CCCC1.[OH-].[Na+]>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]=[C:11]([CH3:14])[N:12]([CH:16]([F:18])[F:17])[CH:13]=1

Participants

5

Reactant 2

HCID 6372ChlorodifluoromethaneHCID 178432508HCID 178432508, compound

Product 1

HCID 22625606HCID 22625606, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

To 1.7 g (7.5 mmol) of 4-(2,4-dichlorophenyl)-2-methyl-1H-imidazole stirring in a mixture of 75 ml of tetrahydrofuran and 8 ml of 50% aqueous sodium hydroxide at room temperature, 8 ml of condensed chlorodifluoromethane was added dropwise from a gas addition funnel. The reaction mixture was stirred at ambient temperature overnight. After partitioning between an excess of ethyl acetate and water, the organic layer was separated, washed with water (3×) and brine, dried over magnesium sulfate, and evaporated in vacuo. The resulting dark red oil was flash chromatographed on silica gel (10:1-5:1-3:1-1:1 hexane/ethyl acetate) to give 940 mg of slightly impure 4-(2,4-dichlorophenyl)-1-difluoromethyl-2-methylimidazole, obtained as an oily solid residue and taken directly to the next step.

Workup

  1. additionwas added dropwise from a gas addition funnel
  2. customAfter partitioning between an excess of ethyl acetate and water
  3. customthe organic layer was separated
  4. washwashed with water (3×) and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customchromatographed on silica gel (10:1-5:1-3:1-1:1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-751297921bee4046b9e8bac78ede45fe
Source dataset
uspto-grants-2002_03
Patent number
US06358885B1

Reaction notes

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