Methanol → Dimethyl 2-bromoterephthalate

HRID 1037131

Reaktionsgleichung

Reaktionsgleichung von HRID 1037131
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[C:11]([O:13][CH3:14])=[O:12])[C:5]([OH:7])=[O:6].O=S(Cl)Cl.[CH3:19]O>>[Br:1][C:2]1[CH:3]=[C:4]([C:5]([O:7][CH3:19])=[O:6])[CH:8]=[CH:9][C:10]=1[C:11]([O:13][CH3:14])=[O:12]

Komponenten

4

Edukt 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 186730263-Bromo-4-(methoxycarbonyl)benzoic acid

Produkt 1

HCID 87741Dimethyl 2-bromoterephthalateAusbeute 98 %

Versuchsvorschrift

To a solution of 3-bromo-4-(methoxycarbonyl)benzoic acid (3.0 g, 11.6 mmol) in MeOH (50 mL) was slowly added SOCl2 (2.76 g, 23.2 mmol) dropwise. After the addition completion, the reaction mixture was refluxed for 5 h. Then MeOH was removed and water was added. It was extracted with EA and the organic layer was washed with aqueous sodium bicarbonate solution, brine, dried over Na2SO4, filtered and concentrated under reduced pressure to give dimethyl 2-bromoterephthalate (3.1 g, yield 98%) as a white solid. It was used without further purification in the next step.

Aufarbeitung

  1. temperatureAfter the addition completion, the reaction mixture was refluxed for 5 h
  2. customThen MeOH was removed
  3. additionwater was added
  4. extractionIt was extracted with EA
  5. washthe organic layer was washed with aqueous sodium bicarbonate solution, brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-41e43f86922a40f58b103a97991c1b65
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08546357B2

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