Water → 5-Bromo-2,4-dimethoxybenzoic acid

HRID 391233

Reaktionsgleichung

Reaktionsgleichung von HRID 391233
[CH3:1][O:2][C:3]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=[O:6].[Br:14]Br.S([O-])([O-])=O.[Na+].[Na+].O>C(O)(=O)C>[Br:14][C:9]1[C:10]([O:12][CH3:13])=[CH:11][C:3]([O:2][CH3:1])=[C:4]([CH:8]=1)[C:5]([OH:7])=[O:6]

Komponenten

6

Edukt 4

HCID 962WaterHCID 70522,4-Dimethoxybenzoic acidHCID 24408BromineHCID 24437Sodium Sulfite

Produkt 1

HCID 135050975-Bromo-2,4-dimethoxybenzoic acidAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel2×

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

2,4-Dimethoxybenzoic acid (30.0 g) was suspended in acetic acid (180 mL). A bromine (27.6 g)/acetic acid (60 mL) solution was slowly added dropwise to the suspension and, after completion of the dropwise addition, the mixture was stirred at 25° C. for 2 hrs, and the termination of the reaction was confirmed by HPLC. An aqueous solution of sodium sulfite (2.10 g) and water (360 mL) was added dropwise to the reaction mixture. After completion of the dropwise addition, the mixture was stirred at 25° C. for 1 hr. Precipitated crystals were filtered, washed 4 times with water (150 mL), and vacuum dried to give 5-bromo-2,4-dimethoxybenzoic acid as white crystals (41.2 g) (96%).

Aufarbeitung

  1. additionafter completion of the dropwise addition
  2. additionAfter completion of the dropwise addition
  3. stirringthe mixture was stirred at 25° C. for 1 hr
  4. customPrecipitated crystals
  5. filtrationwere filtered
  6. washwashed 4 times with water (150 mL), and vacuum
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-ea30f8672b05425dab6dc8b277aca716
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08383819B2

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