Imidazole → 11-Bromomethyl-9,10-dihydro-9,10-ethanoanthracene

HRID 1613225

Reaktionsgleichung

Reaktionsgleichung von HRID 1613225
[CH:1]1[C:14]2[CH:13]3[CH2:15][CH:16]([CH2:17]O)[CH:6]([C:7]4[C:12]3=[CH:11][CH:10]=[CH:9][CH:8]=4)[C:5]=2[CH:4]=[CH:3][CH:2]=1.N1C=CN=C1.ClP(C1C=CC=CC=1)C1C=CC=CC=1.[Br:38]Br>C1(C)C=CC=CC=1>[Br:38][CH2:17][CH:16]1[CH:6]2[C:5]3[CH:4]=[CH:3][CH:2]=[CH:1][C:14]=3[CH:13]([C:12]3[C:7]2=[CH:8][CH:9]=[CH:10][CH:11]=3)[CH2:15]1

Komponenten

6

Edukt 4

HCID 795ImidazoleHCID 24408BromineHCID 66180ChlorodiphenylphosphineHCID 2443799,10-Dihydro-9,10-ethanoanthracene-11-methanol

Produkt 1

HCID 352223811-Bromomethyl-9,10-dihydro-9,10-ethanoanthracene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

9,10-Dihydro-9,10-ethanoanthracene-11-methanol (1.2 gm), imidazole (0.7 gm) and chlorodiphenylphosphine (1.4 gm) were combined in toluene (80 ml) and treated dropwise with bromine (1.0 gm). The mixture was stirred 10 minutes, then extracted with 10% sodium hydroxide (50 ml) and water (50 ml). The toluene was removed on a rotary evaporator and the residue was dissolved in 1:1 methylene chloride/hexane and placed on a silica gel column. The column was eluted with 1:1 methylene chloride/hexane and the eluant removed on a rotary evaporator to give the product.

Aufarbeitung

  1. extractionextracted with 10% sodium hydroxide (50 ml) and water (50 ml)
  2. customThe toluene was removed on a rotary evaporator
  3. dissolutionthe residue was dissolved in 1:1 methylene chloride/hexane
  4. washThe column was eluted with 1:1 methylene chloride/hexane
  5. customthe eluant removed on a rotary evaporator
  6. customto give the product

Quellen und Nachweise

ORD-Eintrag
ord-09b3a976ab4542a1a7d4dc0b7acc113b
Quelldatensatz
uspto-grants-1993_03
Patentnummer
US05192762

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