Tetrabutylammonium Fluoride → 5-Ethoxy-2-fluoro-3-hydroxybenzaldehyde

HRID 2104945Notes

Reaction equation

HRID 2104945 reaction equation
[Si]([O:8][C:9]1[C:10]([F:20])=[C:11]([CH:14]=[C:15]([O:17][CH2:18][CH3:19])[CH:16]=1)[CH:12]=[O:13])(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.CCOC(C)=O>[CH2:18]([O:17][C:15]1[CH:16]=[C:9]([OH:8])[C:10]([F:20])=[C:11]([CH:14]=1)[CH:12]=[O:13])[CH3:19]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 180033743-(Tert-butyldimethylsilyloxy)-5-ethoxy-2-fluorobenzaldehyde

Product 1

HCID 866079345-Ethoxy-2-fluoro-3-hydroxybenzaldehyde

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-(tert-butyldimethylsilyloxy)-5-ethoxy-2-fluorobenzaldehyde (7.25 g, 24.3 mmol), prepared according to WO2003066588 A1, which is incorporated herein by reference, in 50 mL THF at 0° C., was added a 1 M solution of TBAF in THF (24.3 mL, 24.3 mmol). The mixture was stirred for 30 min, then was diluted with EtOAc, washed with H2O (2×) and brine, dried (Na2SO4) and concentrated. The crude product was purified by flash chromatography (0 to 50% EtOAc/hexanes gradient) to afford Intermediate 7.1, contaminated with tetrabutylammonium salts.

Workup

  1. washwashed with H2O (2×) and brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customThe crude product was purified by flash chromatography (0 to 50% EtOAc/hexanes gradient)

Sources & evidence

ORD record
ord-5260fb9f9e634271a3a12db5372495cb
Source dataset
uspto-grants-2009_08
Patent number
US07576098B2

Reaction notes

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