Boron tribromide → Ethyl 6-(benzenesulphonylmethyl)-3-bromo-2-hydroxybenzoate

HRID 2177725Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2177725
B(Br)(Br)Br.[C:5]1([S:11]([CH2:14][C:15]2[C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:19]([O:26]C)[C:18]([Br:28])=[CH:17][CH:16]=2)(=[O:13])=[O:12])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[C:5]1([S:11]([CH2:14][C:15]2[C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:19]([OH:26])[C:18]([Br:28])=[CH:17][CH:16]=2)(=[O:13])=[O:12])[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Komponenten

5

Edukt 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 67107394Ethyl 6-(benzenesulphonylmethyl)-3-bromo-2-methoxybenzoate2×

Produkt 1

HCID 67108192Ethyl 6-(benzenesulphonylmethyl)-3-bromo-2-hydroxybenzoateAusbeute 73,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Boron tribromide (1M solution in DCM, 5.85 ml) was added dropwise to a stirred, cooled solution of ethyl 6-(benzenesulphonylmethyl)-3-bromo-2-methoxybenzoate (Intermediate 61, 2.3 g) in dry DCM (45 ml) at −70° C. The resultant mixture was stirred at −70° C. for 40 minutes, then allowed to warm to room temperature. It was stirred at room temperature for 2 hours then poured into sodium bicarbonate (saturated aqueous solution). The layers were separated and the aqueous layer was extracted with further DCM. The combined organic layers were washed with brine, dried (Na2SO4) and filtered. The filtrate was evaporated to dryness to give ethyl 6-(benzenesulphonylmethyl)-3-bromo-2-hydroxybenzoate (1.64 g) as a white solid.

Aufarbeitung

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with further DCM
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customThe filtrate was evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-9b388b3b5dff40f0b2e05f1f08aa39c7
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09067905B2

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