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

HRID 537117Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 537117
[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-d2837b7e5bb04750a409b00b3941fa57
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08859773B2

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