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Ammonium Chloride → HCID 59557719, Verbindung

HRID 1175325
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1175325
[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH3:16])=[CH:11][CH:10]=2)[C:5]([Cl:17])=[CH:4][C:3]=1[OH:18].CC(C)([O-])C.[K+].FC(F)(F)S(O[CH2:31][CH2:32][O:33][C:34]([F:37])([F:36])[F:35])(=O)=O.[NH4+].[Cl-]>CC#N>[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH3:16])=[CH:11][CH:10]=2)[C:5]([Cl:17])=[CH:4][C:3]=1[O:18][CH2:31][CH2:32][O:33][C:34]([F:37])([F:36])[F:35]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 25517Ammonium ChlorideHCID 106351812-(Trifluoromethoxy)ethyl trifluoromethanesulfonateHCID 23665647Potassium tert-butoxideHCID 59557707HCID 59557707, Verbindung

Produkt 1

HCID 59557719HCID 59557719, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342
Acetonitrile
Lösungsmittel

Versuchsvorschrift

To a solution of 2-bromo-5-chloro-4-(4-ethylbenzyl)phenol (AT) (0.12 g, 0.38 mmol) in anhydrous CH3CN (4 mL), was added potassium tert-butoxide [1.0 M solution in tert-butanol] (380 μL, 0.38 mmol) followed by 2-(trifluoromethoxy)ethyl trifluoromethanesulfonate (0.10 g, 0.38 mmol) [prepared as described in the Journal of Organic Chemistry, 2001, 66, 1061-1063]. The reaction mixture was stirred for 15 h at room temperature, after which saturated NH4Cl was added and the mixture was partitioned between EtOAc and brine. The organic layer was dried with anhydrous Na2SO4, filtered and concentrated. The residue was purified by preparative TLC to give intermediate BP (0.06 g, 36%). 1H-NMR (CDCl3, 300 MHz) δ 7.31 (s, 1H), 7.10 (m, 4H), 6.89 (s, 1H), 4.31 (m, 2H), 4.20 (m, 2H), 3.96 (s, 2H), 2.61 (q, J=7.5 Hz, 2H), 1.22 (t, J=7.5 Hz, 3H).

Aufarbeitung

  1. customprepared
  2. customthe mixture was partitioned between EtOAc and brine
  3. dry with materialThe organic layer was dried with anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by preparative TLC
  7. customto give intermediate BP (0.06 g, 36%)

Quellen und Nachweise

ORD-Eintrag
ord-e581e6b0956e480bb6cac81324d85872
Quelldatensatz
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07838498B2

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