Water → HCID 86602467, compound

HRID 1362597Notes

Reaction equation

HRID 1362597 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-91ec5ddc190a4cb887bf11f4e4e10e88
Source dataset
uspto-grants-2011_02
Patent number
US07880009B2

Reaction notes

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