Imidazole → 3,3-Bisfluoromethyl-1-(4-chlorophenoxy)-1-(imidazol-1-yl)-butan-2-one

HRID 904652Notes

Reaction equation

HRID 904652 reaction equation
[F:1][CH2:2][C:3]([CH2:17][F:18])([CH3:16])[C:4](=[O:15])[CH:5](Br)[O:6][C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=1.[NH:19]1[CH:23]=[CH:22][N:21]=[CH:20]1.O.O.O.O.C1(S(O)(=O)=O)C2C=CC=C(S(O)(=O)=O)C=2C=CC=1>C(#N)C>[F:1][CH2:2][C:3]([CH2:17][F:18])([CH3:16])[C:4](=[O:15])[CH:5]([O:6][C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=1)[N:19]1[CH:23]=[CH:22][N:21]=[CH:20]1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 130194363,3-Bis-fluoromethyl-1-bromo-1-(4-chlorophenoxy)-butan-2-oneHCID 53249422Naphthalene-1,5-disulfonic acid tetrahydrate

Product 1

HCID 130194373,3-Bisfluoromethyl-1-(4-chlorophenoxy)-1-(imidazol-1-yl)-butan-2-oneYield 24%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

61.5 g (0.18 mol) of 3,3-bis-fluoromethyl-1-bromo-1-(4-chlorophenoxy)-butan-2-one were stirred with 27.2 g (0.4 mol) of imidazole in 500 ml of acetonitrile at 45° C. for 4 hours. The solvent was distilled off under a waterpump vacuum, the oil which remained was taken up in 500 ml of methylene chloride, the organic phase was washed twice with 1,000 ml of water and dried over sodium sulphate and the solvent was distilled off. The oil was taken up in acetone, 36 g (0.1 mol) of 1,5-naphthalenedisulphonic acid tetrahydrate were added and the precipitate formed was filtered off. The precipitate (the 1,5-naphthalenedisulphonate of the compound of Example 3) was treated with sodium bicarbonate solution. 14 g (24% of theory) of 3,3-bis-fluoromethyl-1-(4-chlorophenoxy)-1-(imidazol-1-yl)-butan-2-one were obtained as a viscous oil.

Workup

  1. distillationThe solvent was distilled off under a waterpump vacuum
  2. washthe organic phase was washed twice with 1,000 ml of water
  3. dry with materialdried over sodium sulphate
  4. distillationthe solvent was distilled off
  5. customthe precipitate formed
  6. filtrationwas filtered off
  7. additionThe precipitate (the 1,5-naphthalenedisulphonate of the compound of Example 3) was treated with sodium bicarbonate solution

Sources & evidence

ORD record
ord-a72aaebd3481469bbbb89412c50d45e5
Source dataset
uspto-grants-1983_12
Patent number
US04419361

Reaction notes

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