Hydrochloric Acid → [4-[(3-Bromophenoxy)methyl]phenyl]boronic acid

HRID 445116

Reaktionsgleichung

Reaktionsgleichung von HRID 445116
[Br:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([B:23]([OH:25])[OH:24])=[CH:19][CH:18]=1.Cl>CC(C)=O.[I-].[K+].O>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[O:8][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([B:23]([OH:25])[OH:24])=[CH:19][CH:18]=1

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 115633-BromophenolHCID 27355934-(Bromomethyl)phenylboronic acid

Produkt 1

HCID 67975234[4-[(3-Bromophenoxy)methyl]phenyl]boronic acidAusbeute 50,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 4875Potassium IodideKatalysatorHCID 180AcetoneLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

3-bromophenol (0.50 g) was dissolved in acetone, and to the resultant solution, potassium carbonate (1.49 g), potassium iodide (14 mg), and 4-bromomethylphenyl boronic acid (0.62 g) were added, followed by heating the resultant reaction mixture under reflux for 3 hours. The reaction mixture was left to be cooled down, and to the reaction mixture, water was added, and a 2M hydrochloric acid was added to adjust pH of the reaction mixture to 2 to 3, followed by extracting the reaction mixture with ethyl acetate. The organic phase was washed with saturated saline and was dried over anhydrous sodium sulfate. From the organic phase, the solvent was distilled off under reduced pressure, and the resultant residue was purified by silica gel column chromatography to obtain the subject compound (0.45 g) as a colorless solid.

Aufarbeitung

  1. temperatureby heating the resultant
  2. customreaction mixture
  3. temperatureunder reflux for 3 hours
  4. waitThe reaction mixture was left
  5. temperatureto be cooled down
  6. extractionby extracting the reaction mixture with ethyl acetate
  7. washThe organic phase was washed with saturated saline
  8. dry with materialwas dried over anhydrous sodium sulfate
  9. distillationFrom the organic phase, the solvent was distilled off under reduced pressure
  10. customthe resultant residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-863fe1b89fa74fa7a3f641d3e8940456
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08476287B2

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