4-Hydroxybenzaldehyde → 4-(2,2,2-Trifluoroethoxy)benzaldehyde

HRID 877346Notes

Reaction equation

HRID 877346 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].FC(F)(F)S(O[CH2:22][C:23]([F:26])([F:25])[F:24])(=O)=O>CN(C=O)C.O>[F:24][C:23]([F:26])([F:25])[CH2:22][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 10796Cesium carbonateHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonate

Product 1

HCID 47709464-(2,2,2-Trifluoroethoxy)benzaldehyde

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-hydroxyl benzaldehyde (1.1 g, 8.7 mmol) and Cs2CO3 (4.3 g, 13.1 mmol) in DMF (16 mL) was added 2,2,2-trifluoroethyl trifluoromethanesulfonate (1.5 mL, 10.5 mmol). The reaction mixture was stirred at rt for 1 h and then diluted with H2O, followed by extraction with EtOAc. The combined organic layers were dried over Na2SO4, filtered and concentrated. The NMR of the crude product obtained (1.8 g, 100%) was clean. 1H NMR (CDCl3, 400 MHz) δ 9.93 (s, 1H), 7.91-7.87 (m, 2H), 7.09-7.05 (m, 2H), 4.45 (q, J=8.0 Hz, 2H).

Workup

  1. extractionfollowed by extraction with EtOAc
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-bef683288f4c42c8881837823efb72c6
Source dataset
uspto-grants-2015_03
Patent number
US08987310B2

Reaction notes

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