Water → HCID 59703718, compound

HRID 908619Notes

Reaction equation

HRID 908619 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[C:5]#[N:6].O.C(=O)([O-])[O-].[Cs+].[Cs+].Cl[C:19]([F:24])([F:23])C([O-])=O.[Na+]>CN(C)C=O>[F:23][CH:19]([F:24])[O:10][C:9]1[CH:8]=[CH:7][C:4]([C:5]#[N:6])=[CH:3][C:2]=1[F:1]

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 2734985Sodium chlorodifluoroacetateHCID 27829443-Fluoro-4-hydroxybenzonitrile

Product 1

HCID 59703718HCID 59703718, compoundYield 96.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

To a mixed solution of 3-fluoro-4-hydroxybenzonitrile (3.10 g) in N,N-dimethylformamide (31 ml)/water (3.1 ml) were successively added cesium carbonate (10.3 g) and sodium chlorodifluoroacetate (7.93 g). After stirring at 110° C. for 2 hr, the reaction mixture was partitioned by adding toluene and water. The aqueous layer was extracted with toluene, and the combined organic layer was washed with water. The organic layer was dried over anhydrous magnesium sulfate, filtrated, and concentrated under reduced pressure to give the title compound (4.09 g).

Workup

  1. customthe reaction mixture was partitioned
  2. additionby adding toluene and water
  3. extractionThe aqueous layer was extracted with toluene
  4. washthe combined organic layer was washed with water
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. filtrationfiltrated
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-14b473811f5045909c9c350892c03ee9
Source dataset
uspto-grants-2011_09
Patent number
US08017612B2

Reaction notes

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