Indoline → 1-(3-Bromo-4-fluorophenylsulfonyl)indoline

HRID 633576Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 633576
[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].[NH:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][CH2:14]1.C(N(CC)C(C)C)(C)C>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]([S:9]([N:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:15][CH2:14]2)(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[F:8]

Komponenten

5

Edukt 3

HCID 10328IndolineHCID 81531DiisopropylethylamineHCID 218867333-Bromo-4-fluorobenzene-1-sulfonyl chloride

Produkt 1

HCID 867049591-(3-Bromo-4-fluorophenylsulfonyl)indolineAusbeute 67,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of 3-bromo-4-fluorobenzene-1-sulfonyl chloride (2.53 g, 8.33 mmol), indoline (0.933 mL, 8.33 mmol), and N,N-diisopropylethyl-amine (1.60 mL, 9.16 mmol) in tetrahydrofuran (20 mL) was stirred at room temperature for 20 hours. The reaction mixture was partitioned between water and ether. The organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, filtered, and concentrated to a solid residue. Recrystallization from ether and heptane provided the title compound (1.99 g, 67%).

Aufarbeitung

  1. customThe reaction mixture was partitioned between water and ether
  2. washThe organic layer was washed with saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to a solid residue
  6. customRecrystallization from ether and heptane

Quellen und Nachweise

ORD-Eintrag
ord-58e552978f7d41ce9ae0686bd1cd04c8
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09321764B2

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