Dimethylformamide → 2-benzyloxy-4-nitro-S-benzylthiophenol

HRID 1814363

Reaktionsgleichung

Reaktionsgleichung von HRID 1814363
Br[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:25]([SH:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.CN(C=O)C>O>[CH2:12]([O:11][C:3]1[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=1[S:32][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 7509Benzyl mercaptanHCID 11430Potassium CarbonateHCID 2389513-Benzyloxy-4-bromonitrobenzene

Produkt 1

HCID 696927322-benzyloxy-4-nitro-S-benzylthiophenolAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 35.5 g (115.2 mmol) 2-bromo-5-nitro-O-benzylphenol, 26.3 g (190 mmol) potassium carbonate, 15 mL (127 mmol) benzyl mercaptan, and 200 mL DMF were stirred at room temperature 18 h. TLC analysis indicated a complete reaction, so the thick reaction mixture was transferred to a 2 L Erlenmeyer containing 1 L water and the resulting mixture was stirred in a ice/water bath 30 min. The precipitate was filtered, washed with three 300 mL portions of water, dried at 40° C. 18 h under vacuum to give 2-benzyloxy-4-nitro-S-benzylthiophenol 40.5 g (115.2 mmol, 100%) as a yellow solid.

Aufarbeitung

  1. customa complete reaction
  2. stirringthe resulting mixture was stirred in a ice/water bath 30 min
  3. filtrationThe precipitate was filtered
  4. washwashed with three 300 mL portions of water
  5. customdried at 40° C

Quellen und Nachweise

ORD-Eintrag
ord-7030e3cfb9b2419992265cbf5fd67d7d
Quelldatensatz
uspto-grants-2005_04
Patentnummer
US06875765B2

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