Water → HCID 24716039, compound

HRID 469847Notes

Reaction equation

HRID 469847 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10].[Cl:11][C:12]1[CH:17]=[C:16](Cl)[N:15]=[CH:14][N:13]=1.O>C1COCC1.C(OCC)(=O)C>[Cl:11][C:12]1[CH:17]=[C:16]([O:10][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[F:3])[N:15]=[CH:14][N:13]=1

Participants

7

Reactant 4

HCID 962WaterHCID 97072-FluorophenolHCID 24758Sodium hydrideHCID 709434,6-Dichloropyrimidine

Product 1

HCID 24716039HCID 24716039, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

NaH (80 mg, 60%, 3.0 mmol) was added to a solution of 2-fluorophenol (112 mg, 1 mmol) in 10 ml of anhydrous THF, the mixture was stirred for 20 minutes, 4,6-dichloro-pyrimidine (149 mg, 1 mmol) was added and then the reaction mixture was heated at 70° C. for 1 hour. After cooling, 5 ml water was added and ethyl acetate (20 ml) was used to extract the product. The organic layer was dried over sodium sulfate. The solvent was removed by rotovap to give 146 mg of 4-chloro-6-(2-fluorophenoxy)-pyrimidine, yield 65%.

Workup

  1. temperatureAfter cooling
  2. extractionto extract the product
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. customThe solvent was removed by rotovap

Sources & evidence

ORD record
ord-7d8e9942489c4766a8f3cc19f7a7e4e7
Source dataset
uspto-grants-2014_01
Patent number
US08629156B2

Reaction notes

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