Cesium carbonate → 2-(4-Bromo-3-formyl-phenoxy)-4-trifluoromethyl-benzonitrile

HRID 1243689Notes

Reaction equation

HRID 1243689 reaction equation
F[C:2]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[Br:14][C:15]1[CH:22]=[C:21](O)[CH:20]=[CH:19][C:16]=1[CH:17]=[O:18].C(=O)([O-])[O-:25].[Cs+].[Cs+]>CN(C=O)C>[Br:14][C:15]1[CH:22]=[CH:21][C:20]([O:25][C:2]2[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][C:3]=2[C:4]#[N:5])=[CH:19][C:16]=1[CH:17]=[O:18]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 5189732-Fluoro-4-(trifluoromethyl)benzonitrileHCID 110848662-Bromo-4-hydroxybenzaldehyde

Product 1

HCID 219303662-(4-Bromo-3-formyl-phenoxy)-4-trifluoromethyl-benzonitrileYield 972.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

A flask was charged with 2-fluoro-4-(triflouromethyl)benzonitrile (3.78 g, 2 mmol), 2-bromo-4-hydroxybenzaldehyde (4.02 g, 2 mmol), cesium carbonate (6.5 g, 2 mmol) and DMF (40 ml). The mixture was stirred overnight at 40° C. The DMF was evaporated off and the residue was partitioned between ethyl acetate and 5% aqueous sodium hydrogen carbonate. The organic layer was dried with MgSO4. Evaporation yielded a brown oil which solidified to give a brown solid (7.2 g, 97%).

Workup

  1. customThe DMF was evaporated off
  2. customthe residue was partitioned between ethyl acetate and 5% aqueous sodium hydrogen carbonate
  3. dry with materialThe organic layer was dried with MgSO4
  4. customEvaporation
  5. customyielded a brown oil which

Sources & evidence

ORD record
ord-bdc19d6d42e248c1bddc2e7b2f009b18
Source dataset
uspto-grants-2006_10
Patent number
US07119122B2

Reaction notes

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