1-Bromo-1-methylcyclopropane → Cyclopropylmethyl-p-toluenethiosulfonate

HRID 1720074Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1720074
[CH3:1][C:2]1(Br)[CH2:4][CH2:3]1.[S:6]([C:10]1[CH:16]=[CH:15][C:13]([CH3:14])=[CH:12][CH:11]=1)([O-:9])(=[O:8])=[S:7].[K+]>C(O)C>[CH:4]1([CH2:3][O:9][S:6]([C:10]2[CH:16]=[CH:15][C:13]([CH3:14])=[CH:12][CH:11]=2)(=[S:7])=[O:8])[CH2:2][CH2:1]1

Komponenten

4

Edukt 2

HCID 148649461-Bromo-1-methylcyclopropaneHCID 23662126Benzenesulfonothioic acid, 4-methyl-, potassium salt (1:1)

Produkt 1

HCID 86749376Cyclopropylmethyl-p-toluenethiosulfonateAusbeute 72,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a solution of methylcyclopropyl bromide (4.00 g, 29.6 mmol) in ethanol (20.0 mL) was added potassium thiotosylate (10.0 g, 44.4 mmol) and the mixture heated to 90° C. for 10 h. The mixture was then quenched into a 1:1 mixture of H2O (50.0 mL) and diethyl ether (50.0 mL). The layers were separated and the organic layer washed with brine (50.0 mL). The organic layer was then dried with MgSO4 and concentrated in vacuo to yield the title compound as a solid (5.2 g, m.p. 46°-48° C.). 'H NMR (400 MHz, CDCl3) δ 7.816 (d, 2H, J=8.8 Hz), 7.308 (d, 2H, J =8.8 Hz), 2.945 (d, 2H, J=7.6 Hz), 2.451 (s, 3H), 1.010-0.933 (m, 1H), 0.592-0.545 (m, 2H), 0.236-0.197 (m, 2H).

Aufarbeitung

  1. customThe mixture was then quenched into a 1:1 mixture of H2O (50.0 mL) and diethyl ether (50.0 mL)
  2. customThe layers were separated
  3. washthe organic layer washed with brine (50.0 mL)
  4. dry with materialThe organic layer was then dried with MgSO4
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-5a56bb9c9d3942f29a2ffffb13ce6f72
Quelldatensatz
uspto-grants-1996_04
Patentnummer
US05504104

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