Cesium carbonate → HCID 66836578, compound

HRID 1631147Notes

Reaction equation

HRID 1631147 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+].[C:18]([NH:22][CH3:23])([CH3:21])([CH3:20])[CH3:19]>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][N:22]([C:18]([CH3:21])([CH3:20])[CH3:19])[CH3:23]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 84552N-Methyl-tert-butylamineHCID 66836706HCID 66836706, compound

Product 1

HCID 66836578HCID 66836578, 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 206 μl of tert-butylmethylamine 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-b2e09c0116054347aa82d202f6053ed1
Source dataset
uspto-grants-2014_07
Patent number
US08791129B2

Reaction notes

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