Water → HCID 66697112, compound

HRID 2386797Notes

Reaction equation

HRID 2386797 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-7082ef0c022e41939fd1748d72ad3f41
Source dataset
uspto-grants-2012_09
Patent number
US08268820B2

Reaction notes

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