Diisopropylethylamine → HCID 18452898, compound

HRID 1819287Notes

Reaction equation

HRID 1819287 reaction equation
[F:1][C:2]1[CH:9]=[C:8](O)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[CH:11]1[CH:16]=[CH:15][C:14](N(S(C(F)(F)F)(=O)=O)S(C(F)(F)F)(=O)=O)=[CH:13][CH:12]=1.[CH:32](N(CC)C(C)C)(C)C>>[CH2:32]([C:8]1[CH:7]=[CH:6][C:3]([C:4]#[N:5])=[C:2]([F:1])[CH:9]=1)[C:14]1[CH:15]=[CH:16][CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 142176Phenyl triflimideHCID 27346752-Fluoro-4-hydroxybenzonitrile

Product 1

HCID 18452898HCID 18452898, compoundYield 85%

Procedure

To a solution of 16.0 g (116.6 mmol) of 2-fluoro-4-hydroxybenzonitrile and 50.0 g (140.0 mmol) of N-phenyltrifluoromethanesulfonimide in 250 mL of dichlorormethane is added N,N-diisopropylethylamine and the mixture is stirred for 16 hr at room temperature. The mixture is then washed with 10% aqueous sodium bisulfate. The organic portion is separated and the aqueous portion is extracted three times with dichlorormethane. The combined organic portions are dried (Na2SO4), filtered and concentrated in vacuo. Chromatography (silica gel, 50% chloroform/hexane) of the residue affords 26.7 g (85%) of the title compound.

Workup

  1. washThe mixture is then washed with 10% aqueous sodium bisulfate
  2. customThe organic portion is separated
  3. extractionthe aqueous portion is extracted three times with dichlorormethane
  4. dry with materialThe combined organic portions are dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-25f4aec2ff114a63b39983f0ce807bac
Source dataset
uspto-grants-2009_10
Patent number
US07601738B2

Reaction notes

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