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

HRID 1720074노트

반응식

HRID 1720074 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

HCID 86749376Cyclopropylmethyl-p-toluenethiosulfonate수율 72.5%

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
90 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-5a56bb9c9d3942f29a2ffffb13ce6f72
출처 데이터셋
uspto-grants-1996_04
특허 번호
US05504104

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