Water → HCID 86602467, compound

HRID 2247461Notes

Reaction equation

HRID 2247461 reaction equation
[OH-].[Na+].C1(C)C=CC=CC=1.Br[CH2:11][CH2:12][O:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][C:21]=1[F:22])[CH:17]=[O:18].O>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>[F:22][C:21]1[CH:20]=[CH:19][C:16]([CH:17]=[O:18])=[CH:15][C:14]=1[O:13][CH:12]=[CH2:11]

Participants

7

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 14798Sodium HydroxideHCID 866024663-(2-Bromoethoxy)-4-fluorobenzaldehyde

Product 1

HCID 86602467HCID 86602467, compoundYield 49.1%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A 50% sodium hydroxide solution (5 mL) and tetrabutylammonium hydrogen sulfate (859 mg) were added to the toluene (8 mL) solution of 3-(2-bromoethoxy)-4-fluorobenzaldehyde derivative (606 mg) obtained above, and the reaction solution was agitated at room temperature for 1 hour. Water and ethyl acetate were added to the reaction solution after the reaction ended, and the organic layer was separated. The obtained organic layer was washed with a saturated sodium chloride solution, and the solvent was evaporated under reduced pressure after dried over anhydrous magnesium sulfate. The obtained residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate 6:1), and 200 mg (49%) of 4-fluoro-3-vinyloxybenzaldehyde was obtained. The physical properties of the compound are as follows.

Workup

  1. customobtained above, and the reaction solution
  2. customthe organic layer was separated
  3. washThe obtained organic layer was washed with a saturated sodium chloride solution
  4. customthe solvent was evaporated under reduced pressure
  5. dry with materialafter dried over anhydrous magnesium sulfate
  6. customThe obtained residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate 6:1)

Sources & evidence

ORD record
ord-62511e1e23924ead85030a3795486b17
Source dataset
uspto-grants-2010_03
Patent number
US07687640B2

Reaction notes

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