3-Hydroxybenzaldehyde → 3-(2,2-difluoroethoxy)benzaldehyde

HRID 594279Notes

Reaction equation

HRID 594279 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].FC(F)(F)S(O[CH2:16][CH:17]([F:19])[F:18])(=O)=O.C([O-])([O-])=O.[Cs+].[Cs+].O>CN(C=O)C.CCOC(C)=O>[F:18][CH:17]([F:19])[CH2:16][O:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6]

Participants

7

Reactant 4

HCID 1013-HydroxybenzaldehydeHCID 962WaterHCID 10796Cesium carbonateHCID 27740892,2-Difluoroethyl trifluoromethanesulfonate

Product 1

HCID 210714533-(2,2-difluoroethoxy)benzaldehyde

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of commercially available 3-hydroxybenzaldehyde (2.000 g; 16.40 mmol), 2,2-difluoroethyl trifluoromethanesulfonate (3.506 g; 16.40 mmol), and Cs2CO3 (8.004 g; 24.60 mmol) in anh. DMF (30 ml) was stirred at rt, under nitrogen, for 17 h. Water and AcOEt were added and the organic layer was washed with water, dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure affording 3-(2,2-difluoroethoxy)benzaldehyde as a yellow oil. LC-MS (conditions A): tR=0.67 min.; no ionisation.

Workup

  1. washthe organic layer was washed with water
  2. dry with materialdried over anh. MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-8a1a7b2c83ba4b5aaea350eca51a0eae
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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