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Triethylamine → Toluene-4-thiosulfonic acid S-{2-tert-butyl-4-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-5-methyl-phenyl}ester

HRID 1003861
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1003861
[S:1](Br)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].CCN(CC)CC.[C:19]([C:23]1[CH:28]=[C:27]([O:29][CH2:30][CH2:31][O:32][Si:33]([C:36]([CH3:39])([CH3:38])[CH3:37])([CH3:35])[CH3:34])[C:26]([CH3:40])=[CH:25][C:24]=1[SH:41])([CH3:22])([CH3:21])[CH3:20]>C(Cl)(Cl)(Cl)Cl>[C:19]([C:23]1[CH:28]=[C:27]([O:29][CH2:30][CH2:31][O:32][Si:33]([C:36]([CH3:39])([CH3:38])[CH3:37])([CH3:34])[CH3:35])[C:26]([CH3:40])=[CH:25][C:24]=1[S:41][S:1]([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2])([CH3:22])([CH3:21])[CH3:20]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 101308854-Methylbenzene-1-sulfonyl bromide2×HCID 105943112-Tert-butyl-4-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-5-methyl-benzenethiol

Produkt 1

HCID 10791774Toluene-4-thiosulfonic acid S-{2-tert-butyl-4-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-5-methyl-phenyl}ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943
Carbon Tetrachloride
Lösungsmittel
2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a round bottom flask equipped with a magnetic stirrer and an addition funnel were added tosyl bromide (6.07 g, 26.0 mmol), CCl4 (70 mL) and NEt3 (3.59 mL, 26.0 mmol), and this solution was cooled to 0° C. The 2-tert-butyl-4-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-5-methyl-benzenethiol material prepared in Example OOO (4.6 g, 13.0 mmol) was dissolved in CCl4 (70 mL) and added dropwise to the tosyl bromide solution. The addition was complete in 3.5 hours, at which time the ice bath was removed and the reaction stirred at room temperature overnight. The mixture was diluted with CH2Cl2 and washed with saturated NH4Cl and dried (MgSO4). The solvent was then evaporated and the residue was submitted to flash chromatography (1:1 CH2Cl2 :hexane) to yield the title compound. 1H NMR (CDCl3) δ 0.04 (s, 6 H), 0.85 (s, 9 H), 1.20 (s, 9 H), 2.01 (s, 3 H), 2.37 (s, 3 H), 3.93 (t, 2 H), 3.99 (t, 2 H), 6.82 (s, 1 H), 7.03 (s, 1 H), 7.19 (d, 2 H), 7.44 (d, 2 H).

Aufarbeitung

  1. customTo a round bottom flask equipped with a magnetic stirrer and an addition funnel
  2. additionThe addition
  3. customthe ice bath was removed
  4. additionThe mixture was diluted with CH2Cl2
  5. washwashed with saturated NH4Cl
  6. dry with materialdried (MgSO4)
  7. customThe solvent was then evaporated

Quellen und Nachweise

ORD-Eintrag
ord-43e2ecc9a58a4d1c90b63a306f84540a
Quelldatensatz
uspto-grants-2000_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06046355

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