Cesium carbonate → HCID 67227369, compound

HRID 573198Notes

Reaction equation

HRID 573198 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([OH:12])[CH:3]=1.[F:13][C:14]1[CH:21]=[CH:20][CH:19]=[C:18](F)[C:15]=1[C:16]#[N:17].C([O-])([O-])=O.[Cs+].[Cs+]>CS(C)=O>[C:16]([C:15]1[C:14]([F:13])=[CH:21][CH:20]=[CH:19][C:18]=1[O:12][C:4]1[CH:3]=[C:2]([F:1])[CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7])#[N:17]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 746952,6-DifluorobenzonitrileHCID 2775386Methyl 4-fluorosalicylate

Product 1

HCID 67227369HCID 67227369, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of methyl 4-fluoro-2-hydroxybenzoate (10.5 g), 2,6-difluorobenzonitrile (17.17 g) and Cs2CO3 (22.12 g) in dimethyl sulfoxide (150 mL) was heated at 90° C. for 2 hours. After cooling, the reaction mixture was partitioned between water and ethyl acetate. The aqueous layer was extracted with additional ethyl acetate three times. The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated. The solid was triturated with 7:3 hexanes/ethyl acetate (300 mL). The filtrate was concentrated, and the residue was purified by flash chromatography on silica gel eluting from 15%-25% ethyl acetate in hexanes to give the title compound.

Workup

  1. temperatureAfter cooling
  2. customthe reaction mixture was partitioned between water and ethyl acetate
  3. extractionThe aqueous layer was extracted with additional ethyl acetate three times
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe solid was triturated with 7:3 hexanes/ethyl acetate (300 mL)
  9. concentrationThe filtrate was concentrated
  10. customthe residue was purified by flash chromatography on silica gel eluting from 15%-25% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-3b354161347b4d5ab6b16e0d20bb9913
Source dataset
uspto-grants-2015_05
Patent number
US09029404B2

Reaction notes

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