Bromine → Benzyl 2-(2-benzyloxyethyl)-4-bromophenyl ether

HRID 367341Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 367341
[CH2:1]([O:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])(=O)C.[Na+].[Br:30]Br.O.O.O.O.O.O.O.S([O-])([O-])=O.[Na+].[Na+]>C(O)(=O)C.O>[CH2:1]([O:8][CH2:9][CH2:10][C:11]1[CH:16]=[C:15]([Br:30])[CH:14]=[CH:13][C:12]=1[O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

7

Edukt 4

HCID 24408BromineHCID 160916Sodium sulfite heptahydrateHCID 517045Sodium AcetateHCID 23287815Benzyl 2-(2-benzyloxyethyl)phenyl ether

Produkt 1

HCID 23287828Benzyl 2-(2-benzyloxyethyl)-4-bromophenyl ether

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

Benzyl 2-(2-benzyloxyethyl)phenyl ether (159 mg) and 123 mg of sodium acetate was suspended in 2 ml of acetic acid, 29 μl of bromine was added to the suspension with stirring at room temperature, and the mixture was subjected to 1 hour of reaction. Then, a solution of 100 mg of sodium sulfite heptahydrate in 20 ml of water was added, and the mixture was extracted with ethyl acetate. The extract was washed with water, an aqueous saturated sodium bicarbonate solution and water in that order and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the resulting residue was purified by silica gel medium pressure liquid column chromatography (eluent: hexane/methylene chloride=2/1) to give 173 mg of benzyl 2-(2-benzyloxyethyl)-4-bromophenyl ether in an oily form.

Aufarbeitung

  1. customthe mixture was subjected to 1 hour of reaction
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialan aqueous saturated sodium bicarbonate solution and water in that order and then dried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe resulting residue was purified by silica gel medium pressure liquid column chromatography (eluent: hexane/methylene chloride=2/1)

Quellen und Nachweise

ORD-Eintrag
ord-45ef361d1cbc496ba5c28767214a8ced
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06133266

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