Water → HCID 66697112, compound

HRID 2096808Notes

Reaction equation

HRID 2096808 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[CH3:11][C:12]([C:14]1[CH:19]=[CH:18][C:17](F)=[CH:16][C:15]=1[Cl:21])=[O:13].C([O-])([O-])=O.[K+].[K+].O>CC(N(C)C)=O>[C:12]([C:14]1[CH:19]=[CH:18][C:17]([O:10][C:8]2[CH:7]=[CH:6][C:3]([C:4]#[N:5])=[C:2]([Cl:1])[CH:9]=2)=[CH:16][C:15]=1[Cl:21])(=[O:13])[CH3:11]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 5927972-Chloro-4-hydroxybenzonitrileHCID 27365072'-Chloro-4'-fluoroacetophenone

Product 1

HCID 66697112HCID 66697112, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
130 °C

Procedure

To a solution 2-chloro-4-hydroxybenzonitrile (CAS Reg. No. 3336-16-1, 1 g), 2-chloro-4-fluoroacetophenone (CAS Reg. No. 700-35-6, 1.12 g) in DMA (10 ml) was added K2CO3 (1.08 g). The mixture is heated to 110° C. for 2 h and at 130° C. for 1 h. Water was added and the mixture was extracted with EtOAc. The combined organic layers were dried over Na2SO4 and then concentrated to an oil. The residue was purified by flash chromatography (SiO2, 0 to 30% EtOAc/heptane) to give the title compound (780 mg) as light yellow oil. MS (m/e)=306.0 [M+H+].

Workup

  1. extractionthe mixture was extracted with EtOAc
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. concentrationconcentrated to an oil
  4. customThe residue was purified by flash chromatography (SiO2, 0 to 30% EtOAc/heptane)

Sources & evidence

ORD record
ord-ba992f8e9fc24a44bbe75389fdcbd955
Source dataset
uspto-grants-2013_05
Patent number
US08450313B2

Reaction notes

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