Cesium carbonate → HCID 86668205, compound

HRID 1623719Notes

Reaction equation

HRID 1623719 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([F:15])=[C:11]([F:16])[CH:10]=1.[CH:17]([C:19]1[CH:20]=[CH:21][C:22]([OH:28])=[C:23]([CH:27]=1)[C:24]([OH:26])=[O:25])=[O:18]>CN(C)C=O>[F:16][C:11]1[CH:10]=[C:9]([CH2:8][O:28][C:22]2[CH:21]=[CH:20][C:19]([CH:17]=[O:18])=[CH:27][C:23]=2[C:24]([O:26][CH2:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[C:11]([F:16])[CH:10]=2)=[O:25])[CH:14]=[CH:13][C:12]=1[F:15]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 692265-Formylsalicylic acidHCID 5814364-(Bromomethyl)-1,2-difluorobenzene

Product 1

HCID 86668205HCID 86668205, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Cesium carbonate (17.65 g, 54.2 mmol) and 4-(bromomethyl)-1,2-difluorobenzene (5.78 ml, 45.1 mmol) were added to a solution of 5-formyl-2-hydroxybenzoic acid (3 g, 18.06 mmol) in dimethylformamide (100 ml) was added) at room temperature. The mixture was stirred at room temperature overnight. The mixture was then filtered, the dimethylformamide was evaporated and the residue was diluted with ethyl acetate (100 ml) and washed with water (3×50 ml). The organic layer was dried (MgSO4) and evaporated under reduced pressure to give an oil which solidified on standing solidified. The solid was triturated with an 8:1 mixture of hexane/ethyl acetate. The solid was filtered and dried in air under vacuum to yield the title compound as a white solid. 7 g.

Workup

  1. additionwas added) at room temperature
  2. filtrationThe mixture was then filtered
  3. customthe dimethylformamide was evaporated
  4. additionthe residue was diluted with ethyl acetate (100 ml)
  5. washwashed with water (3×50 ml)
  6. dry with materialThe organic layer was dried (MgSO4)
  7. customevaporated under reduced pressure
  8. customto give an oil which
  9. customThe solid was triturated with an 8:1 mixture of hexane/ethyl acetate
  10. filtrationThe solid was filtered
  11. customdried in air under vacuum

Sources & evidence

ORD record
ord-d243d7b223df4a2c88837f50d6a8adf4
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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