4-Toluenesulfonyl chloride → 2-(5-Bromo-7-chlorobenzofuran-2-yl)ethyl 4-methylbenzenesulfonate

HRID 2179399Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2179399
[Br:1][C:2]1[CH:3]=[C:4]([Cl:14])[C:5]2[O:9][C:8]([CH2:10][CH2:11][OH:12])=[CH:7][C:6]=2[CH:13]=1.C(N(CC)CC)C.[C:22]1([CH3:32])[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1>ClCCl>[CH3:32][C:22]1[CH:27]=[CH:26][C:25]([S:28]([O:12][CH2:11][CH2:10][C:8]2[O:9][C:5]3[C:4]([Cl:14])=[CH:3][C:2]([Br:1])=[CH:13][C:6]=3[CH:7]=2)(=[O:30])=[O:29])=[CH:24][CH:23]=1

Komponenten

5

Edukt 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 681096982-(5-Bromo-7-chlorobenzofuran-2-yl)ethanol

Produkt 1

HCID 866680032-(5-Bromo-7-chlorobenzofuran-2-yl)ethyl 4-methylbenzenesulfonateAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of the product of step B (3.5 g, 12.7 mmol) in dichloromethane (30 mL) was added triethylamine (3.7 mL, 25.4 mmol) followed by p-toluenesulfonyl chloride (3.6 mL, 19.05 mmol) at 0° C. The reaction mixture was stirred at ambient temperature for 12 h and concentrated in vacuo. The reaction mixture was quenched with saturated sodium bicarbonate solution, washed with 0.5 N HCl and extracted with ethyl acetate (2×20 mL). The combined organic extracts were dried over Na2SO4 and concentrated in vacuo to give the crude product which was purified by column chromatography (SiO2, 4:1 hexanes/ethyl acetate) providing 2-(5-bromo-7-chlorobenzofuran-2-yl)ethyl 4-methylbenzenesulfonate (5.1 g, 95%) as an off-white solid: 1H NMR (CDCl3, 400 MHz) δ 7.66-7.62 (m, 2H), 7.49 (d, J=2.0 Hz, 1H), 7.36 (d, J=1.6 Hz, 1H), 7.18-7.14 (m, 2H), 6.43 (s, 1H), 4.39 (t, J=6.4 Hz, 2H), 3.14 (t, J=6.0 Hz, 2H), 2.37 (s, 3H).

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. customThe reaction mixture was quenched with saturated sodium bicarbonate solution
  3. washwashed with 0.5 N HCl
  4. extractionextracted with ethyl acetate (2×20 mL)
  5. dry with materialThe combined organic extracts were dried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customto give the crude product which
  8. customwas purified by column chromatography (SiO2, 4:1 hexanes/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-b4846c7ac87f4132ba95a798e79f37d0
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09067949B2

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