Trityl chloride → 2-Bromo-1,4-bis(trityloxymethyl)benzene

HRID 499724Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 499724
[C:1](Cl)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:21][C:22]1[CH:27]=[C:26]([CH2:28][OH:29])[CH:25]=[CH:24][C:23]=1[CH2:30][OH:31].C(N([CH2:37][CH3:38])CC)C>CN(C=O)C.CN(C1C=CN=CC=1)C>[Br:21][C:22]1[CH:27]=[C:26]([CH2:28][O:29][C:1]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:25]=[CH:24][C:23]=1[CH2:30][O:31][C:1]([C:38]1[CH:37]=[CH:19][CH:14]=[CH:15][CH:16]=1)([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Komponenten

6

Edukt 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 18676617(2-Bromo-4-hydroxymethylphenyl)methanol

Produkt 1

HCID 684580852-Bromo-1,4-bis(trityloxymethyl)benzeneAusbeute 18,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Under a nitrogen stream, to a solution of trityl chloride (11.58 g, 41.6 mmol) and (2-bromo-4-hydroxymethylphenyl)methanol (4.1 g, 18.9 mmol) in DMF (12 ml), triethylamine (5.8 ml, 41.6 mmol) and DMAP (369.2 mg, 3.02 mmol) were added and the mixture was stirred for 18 hours at room temperature. The reaction mixture was evaporated under reduced pressure to remove the solvent and then extracted with methylene chloride. The organic layer was washed with water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and then evaporated under reduced pressure to remove the solvent. The resulting residue was purified by silica gel column chromatography (developing solution=ethyl acetate:n-hexane (1:2)) to give the titled compound (2.4 g, 18%).

Aufarbeitung

  1. customThe reaction mixture was evaporated under reduced pressure
  2. customto remove the solvent
  3. extractionextracted with methylene chloride
  4. washThe organic layer was washed with water and saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated under reduced pressure
  7. customto remove the solvent
  8. customThe resulting residue was purified by silica gel column chromatography (developing solution=ethyl acetate:n-hexane (1:2))

Quellen und Nachweise

ORD-Eintrag
ord-8ccba11ff0d24bf381beccbd5c88c6d2
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07767651B2

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