4-Bromophenol → p-Bromophenyl propionate

HRID 1408728

Reaktionsgleichung

Reaktionsgleichung von HRID 1408728
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:16](Cl)(=[O:19])[CH2:17][CH3:18]>CN(C1C=CN=CC=1)C.ClCCl>[C:16]([O:8][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=1)(=[O:19])[CH2:17][CH3:18]

Komponenten

6

Edukt 3

HCID 78084-BromophenolHCID 8471TriethylamineHCID 62324Propionyl chloride

Produkt 1

HCID 90205p-Bromophenyl propionate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

4-Bromophenol (28.4 g, 0.165 mol) and DMAP (0.17 g, 1.4 mmol) were dissolved in dichloromethane (110 mL). The solution was cooled in an ice-bath and triethylamine (24 mL) was added portionwise. Propionyl chloride (16 g, 0.17 mmol) was then added dropwise and the resulting mixture was stirred at room temperature for 2 hrs. The mixture was washed with water, followed by brine, dried and concentrated to give 4-bromophenyl propionate, which was used in the next step without further purification (34 g, 92%). 1H NMR (MeOD, 400 MHz): 1.12-1.24 (m, 3H), 2.57-2.63 (m, 2H), 7.02-7.06 (m, 2H), 7.51-7.55 (m, 2H).

Aufarbeitung

  1. temperatureThe solution was cooled in an ice-bath
  2. washThe mixture was washed with water
  3. customdried
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-e42d71c01fdf4a50aacf3692a668bf12
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08921359B2

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