tert-Butanol → HCID 66816641, Verbindung

HRID 1755073

Reaktionsgleichung

Reaktionsgleichung von HRID 1755073
[C:1]([OH:5])([CH3:4])([CH3:3])[CH3:2].CCN=C=NCCCN(C)C.[Br:17][C:18]1[C:26]([CH3:27])=[CH:25][C:21]([C:22](O)=[O:23])=[CH:20][C:19]=1[CH3:28]>CN(C)C1C=CN=CC=1.ClCCl>[C:1]([O:5][C:22](=[O:23])[C:21]1[CH:25]=[C:26]([CH3:27])[C:18]([Br:17])=[C:19]([CH3:28])[CH:20]=1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

6

Edukt 3

HCID 6386tert-ButanolHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 179371424-Bromo-3,5-dimethylbenzoic acid

Produkt 1

HCID 66816641HCID 66816641, VerbindungAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Dehydrated tert-butanol (0.19 ml, 2.0 mmol), 4-dimethylaminopyridine (81 mg, 0.67 mmol) and EDCI (255 mg, 1.33 mmol) were added to a solution of 4-bromo-3,5-dimethyl-benzoic acid (123 mg, 0.535 mmol) in dichloromethane (1.0 ml) at 0° C., and the mixture was stirred at room temperature for 25 hours. The reaction mixture was diluted with dichloromethane, and the organic layer was washed with water, dried over MgSO4 and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=100/1→50/1) to give 4-bromo-3,5-dimethyl-benzoic acid tert-butyl ester (106 mg, 70%).

Aufarbeitung

  1. washthe organic layer was washed with water
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=100/1→50/1)

Quellen und Nachweise

ORD-Eintrag
ord-fa5c856f9a334d85926eeed27de47450
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09169254B2

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