Boron tribromide → Ethyl 3-hydroxy-4-methylphenylacetate

HRID 2192741

Reaktionsgleichung

Reaktionsgleichung von HRID 2192741
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

step 3—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 (6).

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-d262bb240e7847a582518adfab8ed679
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08329755B2

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