Water → HCID 58423229, compound

HRID 1398026Notes

Reaction equation

HRID 1398026 reaction equation
[F:1][C:2]1[C:9]([OH:10])=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[H-].[Na+].FC(F)(F)S(O[CH2:19][C:20]([F:23])([F:22])[F:21])(=O)=O.O>CN(C=O)C.[Cl-].[Na+].O>[F:1][C:2]1[C:9]([O:10][CH2:19][C:20]([F:23])([F:22])[F:21])=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 196072232-Fluoro-3-hydroxybenzonitrile

Product 1

HCID 58423229HCID 58423229, compoundYield 81.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A stirred solution of 2-fluoro-3-hydroxybenzonitrile (800 mg, 5.83 mmol) in DMF (10 mL) at 0° C. was treated portionwise with NaH (280 mg, 7.00 mmol) (60% oil dispersion). The reaction mixture was then stirred for 0.5 h and 2,2,2-trifluoroethyl trifluoromethanesulfonate (1490 mg, 6.42 mmol) was added. The reaction was allowed to warm to rt overnight with stirring. The reaction mixture was then treated with water (40 mL) and brine (5 mL) and extracted with ethyl acetate (˜50 mL). The organic extract was washed with water, dried over anhydrous Na2SO4, filtered and conc. in vacuo to afford a residue which was purified via silica gel chromatography (10% to 30% ethyl acetate/hexanes) to yield the title compound as a white solid (1040 mg, 81%). 1H NMR (400 MHz, MeOD) δ ppm 7.56 (td, 1 H), 7.47-7.38 (m, 1 H), 7.38-7.24 (m, 1 H), 4.73 (q, 2 H); m/z 220.

Workup

  1. stirringwith stirring
  2. extractionextracted with ethyl acetate (˜50 mL)
  3. extractionThe organic extract
  4. washwas washed with water
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered and conc. in vacuo
  7. customto afford a residue which
  8. customwas purified via silica gel chromatography (10% to 30% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-fee0d2cb4fc144ec9df6cb80da812aba
Source dataset
uspto-grants-2014_12
Patent number
US08901307B2

Reaction notes

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