Sodium hydride → HCID 59713040, compound

HRID 2222753Notes

Reaction equation

HRID 2222753 reaction equation
[CH3:1][O:2][C:3](=[O:17])[CH:4]([C:6]1[CH:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:9]=[C:8]([F:16])[CH:7]=1)[OH:5].[H-].[Na+].[H][H].F[C:23]1[CH:28]=[C:27]([Cl:29])[CH:26]=[CH:25][C:24]=1[C:30]([F:33])([F:32])[F:31]>CN(C)C=O.C(OCC)(=O)C.O>[CH3:1][O:2][C:3](=[O:17])[CH:4]([C:6]1[CH:11]=[C:10]([C:12]([F:14])([F:15])[F:13])[CH:9]=[C:8]([F:16])[CH:7]=1)[O:5][C:25]1[CH:26]=[C:27]([Cl:29])[CH:28]=[CH:23][C:24]=1[C:30]([F:31])([F:32])[F:33]

Participants

8

Reactant 4

HCID 24758Sodium hydrideHCID 142277984-Chloro-2-fluoro-1-(trifluoromethyl)benzeneHCID 59713034HCID 59713034, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 59713040HCID 59713040, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

(3-Fluoro-5-trifluoromethyl-phenyl)-hydroxy-acetic acid methyl ester 91 (0.1 mol) was dissolved in dimethylformamide (100 mL) and sodium hydride (0.1 mol) was added. When hydrogen evolution stopped, a solution of 2-fluoro-4-chloro-1-trifluoromethyl-benzene 92 (0.1 mol) in dimethylformamide (25 mL) was added. The progress of the reaction was monitored by TLC. When the reaction was complete, water and ethyl acetate were added. The organic phase was dried and concentrated, and the residue was chromatographed to afford (3-fluoro-5-trifluoromethyl-phenyl)-(5-chloro-2-trifluoromethyl-phenoxy)-acetic acid methyl ester 93. Basic hydrolysis of this compound, as described in Example 1, then afforded the title compound 94.

Workup

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

Sources & evidence

ORD record
ord-27a8879c3d184bbf9287c3da7578f548
Source dataset
uspto-grants-2008_05
Patent number
US07371888B2

Reaction notes

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