Triethylamine → 2,4-Dichloro-benzoic acid 2-acetyl-5-bromo-phenyl ester

HRID 29251

Reaktionsgleichung

Reaktionsgleichung von HRID 29251
C(N(CC)CC)C.[Br:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:17])[CH3:16])=[C:11]([OH:18])[CH:10]=1.[Cl:19][C:20]1[CH:28]=[C:27]([Cl:29])[CH:26]=[CH:25][C:21]=1[C:22](Cl)=[O:23]>ClCCl>[C:15]([C:12]1[CH:13]=[CH:14][C:9]([Br:8])=[CH:10][C:11]=1[O:18][C:22](=[O:23])[C:21]1[CH:25]=[CH:26][C:27]([Cl:29])=[CH:28][C:20]=1[Cl:19])(=[O:17])[CH3:16]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 666452,4-Dichlorobenzoyl chlorideHCID 107274031-(4-Bromo-2-hydroxyphenyl)ethan-1-one

Produkt 1

HCID 597888752,4-Dichloro-benzoic acid 2-acetyl-5-bromo-phenyl esterAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Triethylamine (14.6 mL, 104.6 mmol) was added to a solution of 1-(4-Bromo-2-hydroxy-phenyl)-ethanone (15.0 g, 96.8 mmol) dissolved in dichloromethane (200 mL). The resulting solution was cooled to 0° C. at which time 2,4-dichloro-benzoyl chloride, dissolved in 50 mL dichloromethane was added dropwise over 30 minutes. The resulting mixture was allowed to warm to ambient temperature and stir at this temperature for an additional 16 hours. After this time, the reaction mixture was concentrated via rotary evaporation and then dissolved in EtOAc and washed twice with water and once with a saturated NaHCO3 solution. The organic portion was dried (MgSO4), filtered and concentrated to give the desired product (22.7 g, 84%) which was used without further purification. 1H-NMR (DMSO) δ 8.18 (d, 1H), 7.96 (d, 1H), 7.82 (s, 1H), 7.64 (m, 3H), 2.53 (s, 3H).

Aufarbeitung

  1. additionwas added dropwise over 30 minutes
  2. concentrationAfter this time, the reaction mixture was concentrated via rotary evaporation
  3. dissolutiondissolved in EtOAc
  4. washwashed twice with water and once with a saturated NaHCO3 solution
  5. dry with materialThe organic portion was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-4fed5d305a384154ad38efb590cc7f20
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07420066B2

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