Bromine → Methyl 6-bromo-3-hydroxy-2-methylbenzoate

HRID 577547Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 577547
[OH:1][C:2]1[C:3]([CH3:12])=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[Br:13]Br.[O-]S([O-])(=S)=O.[Na+].[Na+]>ClCCl>[Br:13][C:9]1[C:4]([C:5]([O:7][CH3:8])=[O:6])=[C:3]([CH3:12])[C:2]([OH:1])=[CH:11][CH:10]=1

Komponenten

5

Edukt 3

HCID 24408BromineHCID 24477Sodium ThiosulfateHCID 12488879Methyl 3-hydroxy-2-methylbenzoate

Produkt 1

HCID 77058981Methyl 6-bromo-3-hydroxy-2-methylbenzoateAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of methyl 3-hydroxy-2-methylbenzoate (114a, 3.557 g, 21.40 mmol) in dichloromethane (100 mL) in a dry ice/acetonitrile bath (˜−45° C.) was added bromine (1.15 mL, 22.5 mmol) dropwise. The reaction was stirred at −45° C. for 2 hours before Na2S2O3 (sat. aq., 2 mL) was added. The reaction mixture was allowed to warm to room temperature. The reaction mixture was diluted with dichloromethane and washed with water. The dichloromethane layer was concentrated under vacuum, and the resulting crude product was purified by column chromatography (0-40% ethyl acetate/heptane) to give methyl 6-bromo-3-hydroxy-2-methylbenzoate (114b, 4.8 g, 92% yield) as a white solid.

Aufarbeitung

  1. additionwas added
  2. washwashed with water
  3. concentrationThe dichloromethane layer was concentrated under vacuum
  4. customthe resulting crude product was purified by column chromatography (0-40% ethyl acetate/heptane)

Quellen und Nachweise

ORD-Eintrag
ord-df2ba9b3fe8045e9b14c73f71d8c0c4d
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09040515B2

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