Triethylamine → 3-bromo-4-(chloromethyl)-1-tert-pentyl-1H-pyrazole

HRID 880914Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 880914
[Br:1][C:2]1[C:6]([CH2:7]O)=[CH:5][N:4]([C:9]([CH2:12][CH3:13])([CH3:11])[CH3:10])[N:3]=1.C(N(CC)CC)C.CS([Cl:25])(=O)=O>ClCCl.C(OCC)(=O)C>[Br:1][C:2]1[C:6]([CH2:7][Cl:25])=[CH:5][N:4]([C:9]([CH2:12][CH3:13])([CH3:11])[CH3:10])[N:3]=1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 67491578(3-bromo-1-tert-pentyl-1H-pyrazol-4-yl)methanol

Produkt 1

HCID 674915603-bromo-4-(chloromethyl)-1-tert-pentyl-1H-pyrazoleAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of (3-bromo-1-tert-pentyl-1H-pyrazol-4-yl)methanol (675 mg, 2.73 mmol) in dichloromethane (10 mL) was cooled to 0° C. Triethylamine (0.53 mL, 3.8 mmol) and methanesulfonyl chloride (0.28 mL, 3.6 mmol) were added. The reaction was stirred at 0° C. for 15 minutes, then warmed to room temperature and stirred for 1.5 hours. The reaction was diluted with ethyl acetate, washed with water and brine, dried over sodium sulfate, filtered, and concentrated to give the title compound (725 mg, 100%) as a clear oil. 1H NMR (400 MHz, CDCl3, δ): 7.48 (s, 1H), 4.47 (s, 2H), 1.86 (q, J=7.48 Hz, 2H), 1.52 (s, 6H), 0.69 (m, 3H).

Aufarbeitung

  1. temperaturewarmed to room temperature
  2. stirringstirred for 1.5 hours
  3. washwashed with water and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-3b898b5b4a8c46b39b86a33d64b339b9
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08993586B2

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