Ammonium Chloride → 5-Bromo-2-(4-methanesulfonylbenzyloxy)pyridine

HRID 42142

Reaktionsgleichung

Reaktionsgleichung von HRID 42142
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[CH3:9][S:10]([C:13]1[CH:20]=[CH:19][C:16]([CH2:17][OH:18])=[CH:15][CH:14]=1)(=[O:12])=[O:11].CC(C)([O-])C.[K+].[Cl-].[NH4+]>O1CCCC1>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([O:18][CH2:17][C:16]2[CH:15]=[CH:14][C:13]([S:10]([CH3:9])(=[O:12])=[O:11])=[CH:20][CH:19]=2)=[N:3][CH:4]=1

Komponenten

6

Edukt 4

HCID 25517Ammonium ChlorideHCID 693532,5-DibromopyridineHCID 3801026(4-Methanesulfonylphenyl)methanolHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 670832565-Bromo-2-(4-methanesulfonylbenzyloxy)pyridineAusbeute 31 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of 2,5-dibromopyridine (474 mg, 2.00 mmol) and 4-(methanesulfonyl)benzyl alcohol (372 mg, 2.00 mmol) in tetrahydrofuran (5 mL) was cooled to −15° C. under N2 and potassium tert-butoxide (1.0M in tetrahydrofuran, 2.2 mL, 2.20 mmol) was added dropwise over 10 minutes. The mixture was stirred at 0° C. for 5.5 hours, poured into saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1) to give the title compound (210 mg, yield 31%).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1)

Quellen und Nachweise

ORD-Eintrag
ord-c78bc94182cb42c48b59f4800f97a3c8
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536176B2

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