Pyrrolidine → 1-((3-Bromo-4-fluorophenyl)sulfonyl)pyrrolidine

HRID 633594Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 633594
[Br:1][C:2]1[CH:3]=[C:4]([S:9](Cl)(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[F:8].[CH:13]([N:16]([CH:19]([CH3:21])C)CC)([CH3:15])C.N1CCCC1>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]([S:9]([N:16]2[CH2:13][CH2:15][CH2:21][CH2:19]2)(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[F:8]

Komponenten

5

Edukt 3

HCID 31268PyrrolidineHCID 81531DiisopropylethylamineHCID 218867333-Bromo-4-fluorobenzene-1-sulfonyl chloride

Produkt 1

HCID 867210711-((3-Bromo-4-fluorophenyl)sulfonyl)pyrrolidineAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 3-bromo-4-fluorobenzene-1-sulfonyl chloride (0.83 g, 2.73 mmol) in tetrahydrofuran (10 mL) under argon was added diisopropylethylamine (0.525 mL, 3.00 mmol) followed by pyrrolidine (0.183 mL, 2.73 mmol). The reaction mixture was stirred at ambient temperature for 2 hours. The reaction mixture was partitioned between diethyl ether and aqueous ammonium chloride. The organic layer was separated, dried over anhydrous magnesium sulfate, filtered, and concentrated. The resulting residue was triturated with diethyl ether/heptane at −20° C. to provide the title compound (0.56 g, 67% yield).

Aufarbeitung

  1. customThe reaction mixture was partitioned between diethyl ether and aqueous ammonium chloride
  2. customThe organic layer was separated
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resulting residue was triturated with diethyl ether/heptane at −20° C.

Quellen und Nachweise

ORD-Eintrag
ord-8f3e01af71bd49008c6f82c4248bdb71
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09321764B2

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