Triethylamine → Isobutyric acid 2-[2-(4-chlorophenyl)-acetyl]-5-fluoro-phenyl ester

HRID 14506Notes

Reaction equation

HRID 14506 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=2[OH:18])=[O:10])=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:26](Cl)(=[O:30])[CH:27]([CH3:29])[CH3:28]>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=2[O:18][C:26](=[O:30])[CH:27]([CH3:29])[CH3:28])=[O:10])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62325Isobutyryl chlorideHCID 687025202-(4-Chlorophenyl)-1-(4-fluoro-2-hydroxy-phenyl)-ethanone

Product 1

HCID 68702502Isobutyric acid 2-[2-(4-chlorophenyl)-acetyl]-5-fluoro-phenyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-(4-chlorophenyl)-1-(4-fluoro-2-hydroxy-phenyl)-ethanone (16.0 g, 60.6 mmol) in CH2Cl2 (300 ml) is added triethylamine (7.4 g, 72.7 mmol). A solution of isobutyryl chloride (7.1 g, 66.6 mmol) in CH2Cl2 (100 ml) is added slowly over 30 min. The reaction mixture is stirred at room temperature for 2 h. The organic phase is washed with 0.5 M HCl, water and brine and dried (MgSO4). The solvent is removed in vacuo, and the product is purified by flash chromatography on silica gel using iso-hexane:ethyl acetate (20:1 to 10:1) as the eluent to give the title compound.

Workup

  1. washThe organic phase is washed with 0.5 M HCl, water and brine
  2. dry with materialdried (MgSO4)
  3. customThe solvent is removed in vacuo
  4. customthe product is purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-e958c84830ae426ab502612169257fb6
Source dataset
uspto-grants-2010_06
Patent number
US07732435B2

Reaction notes

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