Potassium Carbonate → HCID 18440291, compound

HRID 1272188Notes

Reaction equation

HRID 1272188 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][C:3]=1[OH:14].C(=O)([O-])[O-].[K+].[K+].[F:21][C:22]1[CH:23]=[C:24]([CH:27]=[C:28](F)[CH:29]=1)[C:25]#[N:26]>CN1C(=O)CCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][C:3]=1[O:14][C:28]1[CH:29]=[C:22]([F:21])[CH:23]=[C:24]([C:25]#[N:26])[CH:27]=1

Participants

5

Reactant 3

HCID 11430Potassium Carbonate3×HCID 5872043,5-Difluorobenzonitrile2×HCID 58785142HCID 58785142, compound

Product 1

HCID 18440291HCID 18440291, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of ethyl 4-chloro-3-hydroxyphenylacetate (34a; 1.4 g; 6.5 mmol) and NMP (13 mL) was added potassium carbonate (2.7 g; 19.6 mmol) and 1.2 g of 3,5-difluorobenzonitrile (1.2 g; 8.5 mmol). The reaction mixture was heated to 120° C. and monitored by TLC. After 3.5 h an additional 0.9 g of K2CO3 was added and at 5.5 h an additional 0.9 g of K2CO3 and 0.3 g of 3,5-difluorobenzonitrile was added. After 8 h of heating the reaction was cooled to rt and the reaction mixture was filtered through a pad of CELITE® and the solid cake was washed well with EtOAc. The filtrate was washed with 2 portions of 2N HCl, 1N NaOH, water and brine. The organic extract was dried (MgSO4), filtered and evaporated to yield 1.3 g of the ether 35a.

Workup

  1. additionwas added
  2. temperatureAfter 8 h of heating the reaction
  3. temperaturewas cooled to rt
  4. filtrationthe reaction mixture was filtered through a pad of CELITE®
  5. washthe solid cake was washed well with EtOAc
  6. washThe filtrate was washed with 2 portions of 2N HCl, 1N NaOH, water and brine
  7. extractionThe organic extract
  8. dry with materialwas dried (MgSO4)
  9. filtrationfiltered
  10. customevaporated
  11. customto yield 1.3 g of the ether 35a

Sources & evidence

ORD record
ord-88e7035059594884b39b1859f84347a4
Source dataset
uspto-grants-2007_04
Patent number
US07208509B2

Reaction notes

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