Water → Methyl 3-methoxy4-(5-nitrobenzo[b]thien-3-ylmethyl)benzoate

HRID 275135

Reaktionsgleichung

Reaktionsgleichung von HRID 275135
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]2[S:8][CH:9]=[CH:10][C:6]=2[CH:5]=1)([O-:3])=[O:2].Br[CH2:14][C:15]1[CH:24]=[CH:23][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][C:16]=1[O:25][CH3:26].O>ClCCl>[CH3:26][O:25][C:16]1[CH:17]=[C:18]([CH:23]=[CH:24][C:15]=1[CH2:14][C:10]1[C:6]2[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:12]=[CH:11][C:7]=2[S:8][CH:9]=1)[C:19]([O:21][CH3:22])=[O:20]

Komponenten

5

Edukt 3

HCID 962WaterHCID 2759828Methyl 4-(bromomethyl)-3-methoxybenzoateHCID 124140845-Nitro-1-benzothiophene

Produkt 1

HCID 14763112Methyl 3-methoxy4-(5-nitrobenzo[b]thien-3-ylmethyl)benzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Stannic chloride (0.41 g.) was added to a stirred solution of 5-nitrobenzo[b]thiophene (0.28 g.) and methyl 4-bromomethyl-3-methoxybenzoate (B) (0.61 g.) in dichloromethane (5 ml.). The mixture was heated under reflux for 18 hours. The cooled mixture was poured into water (10 ml.) and extracted with dichloromethane (2×20 ml.). The combined extracts were dried (MgSO4) and evaporated. The oil was purified by flash chromatography on silica gel (100 ml.) eluting with 1:9 v/v ethyl acetate:hexane. The solid obtained was crystallized from hexane to give methyl 3-methoxy-4-(5-nitrobenzo[b]thien-3-ylmethyl)benzoate (I) as a solid (0.16 g., 30%); NMR: (250 MHz, CDCl3): 3.92(s, 3H, OCH3), 3.98(s,3H, OCH3), 4.28(s,2H, CH2 --Ar), 7.15 (d,1H), 7.22(s,1H), 7.56(m,2H), 7.93(d,1H), 8.19(dd, 1H); 8.73(d,1H).

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 18 hours
  3. extractionextracted with dichloromethane (2×20 ml.)
  4. dry with materialThe combined extracts were dried (MgSO4)
  5. customevaporated
  6. customThe oil was purified by flash chromatography on silica gel (100 ml.)
  7. washeluting with 1:9 v/v ethyl acetate
  8. customThe solid obtained
  9. customwas crystallized from hexane

Quellen und Nachweise

ORD-Eintrag
ord-369a7bbec6e046beb4ca9cbf490165aa
Quelldatensatz
uspto-grants-1995_02
Patentnummer
US05391758

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