Cesium carbonate → HCID 86668207, compound

HRID 1623723Notes

Reaction equation

HRID 1623723 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=1.[CH:16]([C:18]1[CH:19]=[CH:20][C:21]([OH:27])=[C:22]([CH:26]=1)[C:23]([OH:25])=[O:24])=[O:17]>CN(C)C=O>[F:15][C:12]1[CH:13]=[CH:14][C:9]([CH2:8][O:27][C:21]2[CH:20]=[CH:19][C:18]([CH:16]=[O:17])=[CH:26][C:22]=2[C:23]([O:25][CH2:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)=[O:24])=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 680214-Fluorobenzyl bromideHCID 692265-Formylsalicylic acid

Product 1

HCID 86668207HCID 86668207, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Cesium carbonate (11.77 g, 36.1 mmol) and 1-(bromomethyl)-4-fluorobenzene (1.50 ml, 12.04 mmol) were added to a solution of 5-formyl-2-hydroxybenzoic acid (2 g, 12.04 mmol) in dimethylformamide (100 m) at room temperature. The mixture was stirred at room temperature overnight. The mixture was 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. 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. 4.09 g.

Workup

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

Sources & evidence

ORD record
ord-7d9cf8a677f34936920b0c3ed270a848
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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