Bromine → 2-Bromo-3',4'-bis(pivaloyloxy)acetophenone

HRID 2417884

Reaktionsgleichung

Reaktionsgleichung von HRID 2417884
[C:1]([O:7][C:8]1[CH:9]=[C:10]([C:21](=[O:24])[CH2:22]C)[CH:11]=[CH:12][C:13]=1[O:14][C:15](=[O:20])[C:16]([CH3:19])([CH3:18])[CH3:17])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].C(OC1C=C(C(=O)C)C=CC=1OC(=O)C(C)(C)C)(=O)C(C)(C)C.OC1C=C(C(=O)CC)C=CC=1O.C(Cl)(=O)C(C)(C)C.[Br:67]Br>C(N(CC)CC)C>[Br:67][CH2:22][C:21]([C:10]1[CH:11]=[CH:12][C:13]([O:14][C:15](=[O:20])[C:16]([CH3:19])([CH3:18])[CH3:17])=[C:8]([O:7][C:1](=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3])[CH:9]=1)=[O:24]

Komponenten

7

Edukt 5

HCID 24408BromineHCID 62493Pivaloyl chlorideHCID 962673',4'-DihydroxypropiophenoneHCID 128761863',4'-Bis(pivaloyloxy)acetophenoneHCID 135902443',4'-Bis(pivaloyloxy)propiophenone

Produkt 1

HCID 128761872-Bromo-3',4'-bis(pivaloyloxy)acetophenone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

3',4'-Bis(pivaloyloxy)propiophenone was first prepared as a mobile liquid (63.6 g.), in a similar manner to 3',4'-bis(pivaloyloxy)acetophenone in Example 1, starting from 3', 4'-dihydroxypropiophenone (40 g.), pivaloylchloride (63.3 ml.) and triethylamine (73.2 ml.). This mobile liquid (40.1 g.) was then reacted with bromine (7.2 ml.) in a similar manner to that used in Example 1 to obtained 2-bromo-3',4'-bis(pivaloyloxy)acetophenone. The crude bromo compound thus obtained was purified by dry column chromatography on silica gel as described in Example 1 to give pure 2-bromo-3',4'-bis(pivaloyloxy)propiophenone as a solid (18.4 g), m.p. 58°-60° C.

Quellen und Nachweise

ORD-Eintrag
ord-691ae03f5f104570b9123ff88db0b45c
Quelldatensatz
uspto-grants-1984_09
Patentnummer
US04470997

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