4-Toluenesulfonyl chloride → 2,2-Difluoroprop-1-yl toluene-4-sulphonate

HRID 222591Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 222591
[F:1][C:2]([F:6])([CH3:5])[CH2:3][OH:4].C(N(CC)CC)C.[C:14]1([CH3:24])[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=1>ClCCl>[F:1][C:2]([F:6])([CH3:5])[CH2:3][O:4][S:20]([C:17]1[CH:18]=[CH:19][C:14]([CH3:24])=[CH:15][CH:16]=1)(=[O:22])=[O:21]

Komponenten

5

Edukt 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 133948182,2-Difluoropropanol

Produkt 1

HCID 567765062,2-Difluoroprop-1-yl toluene-4-sulphonateAusbeute 76,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 2,2-difluoropropanol (0.50 g, 5.20 mmol) in dichloromethane (52.0 mL) and triethylamine (0.50 g, 0.73 mL, 5.20 mmol) at 0° C. is added p-toluenesulfonyl chloride (0.99 g, 5.20 mmol). The mixture is allowed to slowly warm to room temperature over 24 h. The mixture is concentrated and is partitioned between diethyl ether and water. The organic layer is washed with water and brine, dried over magnesium sulfate, filtered, and concentrated to dryness. The material is purified over silica gel to obtain 1.0 g of the title compound as clear crystals. MS (m/z) 250 (M+1).

Aufarbeitung

  1. concentrationThe mixture is concentrated
  2. customis partitioned between diethyl ether and water
  3. washThe organic layer is washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. customThe material is purified over silica gel

Quellen und Nachweise

ORD-Eintrag
ord-edbc2b3c4a1a4cb4a7af8d259f0756b6
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08207344B2

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