4-Hydroxybenzaldehyde → 4-(3,3,3-Trifluoropropoxy)benzaldehyde

HRID 629179Notes

Reaction equation

HRID 629179 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[F:10][C:11]([F:16])([F:15])[CH2:12][CH2:13]I.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C)C=O>[F:10][C:11]([F:16])([F:15])[CH2:12][CH2:13][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 962WaterHCID 10796Cesium carbonateHCID 1561651,1,1-Trifluoro-3-iodopropane

Product 1

HCID 583421884-(3,3,3-Trifluoropropoxy)benzaldehydeYield 2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of 4-hydroxybenzaldehyde (740 mg, 6.0 mmol) and (3,3,3-trifluoro)-1-iodopropane (2.67 g, 12.0 mmol) in 10 mL dimethylformamide was added cesium carbonate (4.0 g, 12.3 mmol) and the resulting slurry stirred vigorously at 85° C. for 24 h. After cooling to room temperature the reaction mixture was poured into 100 mL water. Organics were extracted with ether (3×75 mL), dried over magnesium sulfate, filtered and concentrated. The residue was subjected to chromatography on silica gel (30% ethyl acetate in hexanes) to give 4-(3,3,3-trifluoropropoxyl)benzaldehyde (24 mg, 2%). Used without further characterization.

Workup

  1. temperatureAfter cooling to room temperature the reaction mixture
  2. extractionOrganics were extracted with ether (3×75 mL)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-19e517ecc7ff4ad6a304627158bbc676
Source dataset
uspto-grants-2016_04
Patent number
US09315495B2

Reaction notes

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