Sodium hydride → Bis(4-trifluoromethylthiobenzyl)ether

HRID 1358737

Reaktionsgleichung

Reaktionsgleichung von HRID 1358737
[H-].[Na+].[F:3][C:4]([F:15])([F:14])[S:5][C:6]1[CH:13]=[CH:12][C:9]([CH2:10][OH:11])=[CH:8][CH:7]=1.[F:16][C:17]([F:28])([F:27])[S:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23]Br)=[CH:21][CH:20]=1>C1COCC1>[F:15][C:4]([F:14])([F:3])[S:5][C:6]1[CH:13]=[CH:12][C:9]([CH2:10][O:11][CH2:23][C:22]2[CH:25]=[CH:26][C:19]([S:18][C:17]([F:28])([F:16])[F:27])=[CH:20][CH:21]=2)=[CH:8][CH:7]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 27778704-((Trifluoromethyl)thio)benzenemethanolHCID 27778824-(Trifluoromethylthio)benzyl bromide

Produkt 1

HCID 12112481Bis(4-trifluoromethylthiobenzyl)etherAusbeute 87,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Sodium hydride (65 mg 60% dispersion oil, 1.58 mmol) was added to a solution of 4-(trifluoromethylthio)benzyl alcohol (300 mg, 1.44 mmol) in THF (10 mL) at rt. After stirring for 10 min, to the mixture was added 4-(trifluoromethylthio)benzyl bromide (410 mg, 1.51 mmol), stirring was continued overnight. The reaction was quenched with saturated ammonium chloride solution, extracted with EtOAc, washed with water and dried to give 0.5 g (85%) of bis(4-trifluoromethylthiobenzyl) ether as a yellow oil. 1HNMR (360 MHz, DMSO-d6) δ 7.70 (d, J=8.1 Hz, 4H), 7.53 (d, J=8.1 Hz, 4H), 4.65 (s, 4H, CH2OCH2). MS-EI m/z 398 [M+].

Aufarbeitung

  1. stirringstirring
  2. waitwas continued overnight
  3. customThe reaction was quenched with saturated ammonium chloride solution
  4. extractionextracted with EtOAc
  5. washwashed with water
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-b6758ded59d74e05aee992c35e218b2b
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06596772B1

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