HCID 68430396, compound → HCID 68534886, compound

HRID 2266992Notes

Reaction equation

HRID 2266992 reaction equation
[I:1][CH2:2][C:3]1[CH:17]=[CH:16][C:6]([O:7][C:8]2[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=2)[C:11]#[N:12])=[CH:5][CH:4]=1.[OH:18][C:19]1[C:24]([C:25]([F:28])([F:27])[F:26])=[C:23]([OH:29])[CH:22]=[CH:21][C:20]=1[C:30](=[O:32])[CH3:31]>CN(C)C=O>[I:1][CH2:2][C:3]1[CH:17]=[CH:16][C:6]([O:7][C:8]2[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=2)[C:11]#[N:12])=[CH:5][CH:4]=1.[C:30]([C:20]1[CH:21]=[CH:22][C:23]([O:29][CH2:2][C:3]2[CH:17]=[CH:16][C:6]([O:7][C:8]3[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=3)[C:11]#[N:12])=[CH:5][CH:4]=2)=[C:24]([C:25]([F:27])([F:26])[F:28])[C:19]=1[OH:18])(=[O:32])[CH3:31]

Participants

5

Reactant 2

HCID 68430396HCID 68430396, compoundHCID 68535874HCID 68535874, compound2×

Product 2

HCID 68534886HCID 68534886, compoundYield 100.9%HCID 68535874HCID 68535874, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
60 °C

Procedure

3-(4-Iodomethyl-phenoxy)-benzonitrile is prepared by an analogous procedure described in Preparation 43. Add half of a solution of 3-(4-iodomethyl-phenoxy)-benzonitrile (470 mg, 1.4 mmol) in anhydrous dimethylformamide (10 mL) to 1-(2,4-dihydroxy-3-trifluoromethyl-phenyl)-ethanone (300 mg, 1.4 mmol) and Li2CO3 (228 mg, 3.1 mmol) in anhydrous dimethylformamide (18 mL)dimethylformamide. Heat the reaction mixture to 60° C. and stir for 1 h. Add the other half of the 3-(4-iodomethyl-phenoxy)-benzonitrile solution to the reaction mixture. Stirred at 60° C. for an additional 1 h, cool to room temperature, and quench with water (75 mL). Extract the aqueous mixture with ethyl acetate (3×75 mL). Combine the organic layers, wash with brine, dry over sodium sulfatesodium sulfate, and concentrate. Purify the residue by flash column chromatography using 50% ethyl acetate/hexane as the eluent to give the title compound (302 mg, 50%). LC-MS (m/e): 426 (M−1)

Workup

  1. customdescribed in Preparation 43
  2. stirringStirred at 60° C. for an additional 1 h
  3. temperaturecool to room temperature
  4. customquench with water (75 mL)
  5. extractionExtract the aqueous mixture with ethyl acetate (3×75 mL)
  6. washCombine the organic layers, wash with brine
  7. dry with materialdry over sodium sulfatesodium sulfate
  8. concentrationconcentrate
  9. customPurify the residue by flash column chromatography

Sources & evidence

ORD record
ord-5ba2a84828334000a0d8252b6fcc246a
Source dataset
uspto-grants-2010_12
Patent number
US07858646B2

Reaction notes

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