Ethyl Acetate → HCID 25260103, compound

HRID 2222752Notes

Reaction equation

HRID 2222752 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.[CH2:12]([O:14][C:15](=[O:28])[CH:16]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=1)Br)[CH3:13].C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C)C=O.[Cl-].[Na+].O>[CH2:12]([O:14][C:15](=[O:28])[CH:16]([O:9][C:6]1[CH:5]=[CH:4][C:3]([C:2]([F:10])([F:11])[F:1])=[CH:8][CH:7]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:26])([F:27])[F:25])[CH:19]=1)[CH3:13]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 678744-(Trifluoromethyl)phenolHCID 12717579HCID 12717579, compound

Product 1

HCID 25260103HCID 25260103, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

4-Trifluoromethylphenol (43.8 g, 0.27 mol), bromo-(3-trifluoromethyl-phenyl)-acetic acid ethyl ester 79 (70 g, 0.225 mol) and potassium carbonate (56 g, 0.405 mol) were stirred in dimethylformamide (200 mL) for 16 hours. Ethyl acetate and brine were added and the organic phase was dried and concentrated. The residue was chromatographed to afford (4-trifluoromethyl-phenoxy)-(3-trifluoromethyl-phenyl)-acetic acid ethyl ester, 80, as an oil. This material was dissolved in tetrahydrofuran/methanol (400 mL/300 mL) and 1N lithium hydroxide (300 mL) was added. After 1 hour, 1N hydrochloric acid (300 mL) was added. The mixture was extracted with ethyl acetate. The extract was dried and concentrated to afford the title compound 39 as a white solid. 1H NMR (d6-DMSO) δ 7.88-7.85 (m, 2H), 7.62-7.55 (m, 4H), 7.09 (d, 2H), 5.52 (s, 1H).

Workup

  1. customthe organic phase was dried
  2. concentrationconcentrated
  3. customThe residue was chromatographed

Sources & evidence

ORD record
ord-92079b88dfd242f4a0db16c1be136bb2
Source dataset
uspto-grants-2008_05
Patent number
US07371888B2

Reaction notes

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