Tert-butyl(4-chloro-2-ethynylphenoxy)acetate → Tert-butyl(4-chloro-2-{[2-fluoro-5-(isopropylsulfonyl)phenyl]ethynyl}phenoxy)acetate

Reaktionsgleichung

FC1C=CC(S(CCC)(=O)=O)=CC=1C#C[Si](C)(C)C.[C:20]([O:24][C:25](=[O:37])[CH2:26][O:27][C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][C:29]=1[C:35]#[CH:36])([CH3:23])([CH3:22])[CH3:21].Br[C:39]1[CH:44]=[C:43]([S:45]([CH:48]([CH3:50])[CH3:49])(=[O:47])=[O:46])[CH:42]=[CH:41][C:40]=1[F:51]>>[C:20]([O:24][C:25](=[O:37])[CH2:26][O:27][C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][C:29]=1[C:35]#[C:36][C:41]1[CH:42]=[C:43]([S:45]([CH:48]([CH3:49])[CH3:50])(=[O:46])=[O:47])[CH:44]=[CH:39][C:40]=1[F:51])([CH3:23])([CH3:22])[CH3:21]

Komponenten

Edukt 3

HCID 56594381Tert-butyl(4-chloro-2-ethynylphenoxy)acetate2×

HCID 58521874{[2-Fluoro-5-(propylsulfonyl)phenyl]ethynyl}trimethyl silane

HCID 585219702-Bromo-1-fluoro-4-(isopropylsulfonyl)benzene2×

Produkt 1

HCID 58522040Tert-butyl(4-chloro-2-{[2-fluoro-5-(isopropylsulfonyl)phenyl]ethynyl}phenoxy)acetate

Versuchsvorschrift

Following the general method as outlined in Intermediate 107, starting from (4-chloro-2-ethynyl-phenoxy)-acetic acid tert-butyl ester (Intermediate 3) and 2-bromo-1-fluoro-4-(isopropylsulfonyl)benzene (Intermediate 128), the title compound was obtained as a white solid after purification by flash column chromatography (silica), eluting with cyclohexane containing increasing amounts of EtOAc.