4-Hydroxybenzaldehyde → 4-(2-Fluoroethoxy)benzaldehyde

HRID 339514Notes

Reaction equation

HRID 339514 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[F:29][CH2:30][CH2:31]O.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[F:29][CH2:30][CH2:31][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 97372-FluoroethanolHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylate

Product 1

HCID 150586494-(2-Fluoroethoxy)benzaldehydeYield 40.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of 4-hydroxybenzaldehyde (1.45 g, 11.9 mmol), triphenylphosphine (6.87 g, 26.2 mmol) and 2-fluoroethanol (1.68 g, 26.2 mmol) in dry THF (70 ml) at 0° C., was added DIAD (5.29 g, 26.2 mmol) dropwise. The reaction mixture was stirred at 0° C. for 1 h then allowed to rise to room temperature and stirred for 48 h. The solvent was removed under reduced pressure and the residue was purified by flash chromatography (5:1 DCM/Hexane) to give the title compound (0.807 g, 40%) as a colourless solid.

Workup

  1. customto rise to room temperature
  2. stirringstirred for 48 h
  3. customThe solvent was removed under reduced pressure
  4. customthe residue was purified by flash chromatography (5:1 DCM/Hexane)

Sources & evidence

ORD record
ord-12596ad63e034068bc35439fa725b6d2
Source dataset
uspto-grants-2014_11
Patent number
US08895313B2

Reaction notes

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