Cesium fluoride → HCID 88504235, compound

HRID 1772869Notes

Reaction equation

HRID 1772869 reaction equation
[F-].[Cs+].[Cl:3][C:4]1[C:9]([CH:10]=[O:11])=[C:8]([F:12])[C:7]([Si](C)(C)C)=[C:6]([F:17])[CH:5]=1>CN(C)C=O.CCCCCCC.O>[Cl:3][C:4]1[CH:5]=[C:6]([F:17])[CH:7]=[C:8]([F:12])[C:9]=1[CH:10]=[O:11]

Participants

6

Reactant 2

HCID 25953Cesium fluorideHCID 866138416-Chloro-2,4-difluoro-3-trimethylsilylbenzaldehyde

Product 1

HCID 88504235HCID 88504235, compoundYield 40.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolventHCID 8900HeptaneSolvent

Procedure

CsF (approximately 0.2 g) was added to a mixture of crude 6-chloro-2,4-difluoro-3-(trimethylsilyl)benzaldehyde (10.5 g, approximately 42 mmol) in dimethylformamide (15 mL)/H2O (2 mL). After stirring for 10 min the reaction was diluted with heptane and H2O. The phases were separated and the aqueous extracted with further heptane. The combined organic layers were washed with H2O, dried over MgSO4 and concentrated in vacuo to a yellow oil. Purification by column chromatography (1:4 EtOAc:heptane) followed by trituration with pentane gave the title compound as a white solid (3.0 g, 17.0 mmol).

Workup

  1. customThe phases were separated
  2. extractionthe aqueous extracted with further heptane
  3. washThe combined organic layers were washed with H2O
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo to a yellow oil
  6. customPurification by column chromatography (1:4 EtOAc:heptane)

Sources & evidence

ORD record
ord-7e7d287b5825465f9bc177a59995724c
Source dataset
uspto-grants-2016_02
Patent number
US09249160B2

Reaction notes

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