Boron tribromide → Ethyl 3-hydroxy-4-methylphenylacetate

HRID 1272186

Reaktionsgleichung

Reaktionsgleichung von HRID 1272186
C[O:2][C:3]1[CH:4]=[C:5]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:6]=[CH:7][C:8]=1[CH3:9].B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[C:5]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:6]=[CH:7][C:8]=1[CH3:9]

Komponenten

4

Edukt 2

HCID 25134Boron tribromideHCID 21079756Ethyl 3-methoxy-4-methylphenylacetate

Produkt 1

HCID 21079755Ethyl 3-hydroxy-4-methylphenylacetateAusbeute 90,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a solution of 4c (2.2 g; 8.0 mmol) and 250 mL CH2Cl2 cooled to −78° C. was added dropwise via syringe BBr3 (9.8 mL; 0.104 mol). After 1 h at −78° C. the reaction was stirred for 4 h in an ice-water bath. The reaction mixture was recooled to −78° C. and the reaction quenched aqueous NaHCO3 then warmed to rt and the organic phase washed with water, saturated NaHCO3 and brine. The organic phase was dried (MgSO4) and the solvent evaporated to afford 1.4 g of ethyl 3-hydroxy-4-methylphenylacetate (5a).

Aufarbeitung

  1. customwas recooled to −78° C.
  2. customthe reaction quenched aqueous NaHCO3
  3. temperaturethen warmed to rt
  4. washthe organic phase washed with water, saturated NaHCO3 and brine
  5. dry with materialThe organic phase was dried (MgSO4)
  6. customthe solvent evaporated

Quellen und Nachweise

ORD-Eintrag
ord-8b01cabdcdb2463cb7a27ad655da719a
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07208509B2

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