Cesium carbonate → HCID 89675002, compound

HRID 1631143Notes

Reaction equation

HRID 1631143 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1[CH2:10]Cl.C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:18][NH:19][CH2:20][CH3:21]>C(#N)C>[Br:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1[CH2:10][CH2:18][NH:19][CH2:20][CH3:21]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 12219N-MethylethylamineHCID 66836706HCID 66836706, compound

Product 1

HCID 89675002HCID 89675002, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

200 mg of 1-bromo-2-chloromethyl-4,5-difluorobenzene are dissolved in 5 ml of acetonitrile. 540 mg of caesium carbonate and 146 μl of methylethylamine are added, and the mixture is stirred at 80° C. for 16 h. After cooling to 25° C., the mixture is filtered, and the filtrate is evaporated to dryness. The residue is taken up in 5 ml of ethyl acetate, the solution is washed with 5 ml of 2N sodium hydroxide solution, and the combined organic phases are dried over sodium sulfate. After filtration, the filtrate is evaporated to dryness, after which the product is isolated as oil.

Workup

  1. temperatureAfter cooling to 25° C.
  2. filtrationthe mixture is filtered
  3. customthe filtrate is evaporated to dryness
  4. washthe solution is washed with 5 ml of 2N sodium hydroxide solution
  5. dry with materialthe combined organic phases are dried over sodium sulfate
  6. filtrationAfter filtration
  7. customthe filtrate is evaporated to dryness
  8. customafter which the product is isolated as oil

Sources & evidence

ORD record
ord-e251aca34e1047fb9bf8ddb7c24ca5b4
Source dataset
uspto-grants-2014_07
Patent number
US08791129B2

Reaction notes

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