1-Bromo-4-fluoro-5-methanesulfonyl-2-methyl-benzene → Tert-butyl(4-chloro-2-{[4-fluoro-2-methyl-5-(methylsulfonyl)phenyl]ethynyl}phenoxy)acetate

HRID 2390200Notes

Reaction equation

HRID 2390200 reaction equation
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]([CH3:48])(=[O:47])=[O:46])[C:42]([F:49])=[CH:41][C:40]=1[CH3:50]>>[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:39]1[CH:44]=[C:43]([S:45]([CH3:48])(=[O:47])=[O:46])[C:42]([F:49])=[CH:41][C:40]=1[CH3:50])([CH3:23])([CH3:22])[CH3:21]

Participants

4

Reactant 3

HCID 98382241-Bromo-4-fluoro-5-methanesulfonyl-2-methyl-benzeneHCID 56594381Tert-butyl(4-chloro-2-ethynylphenoxy)acetate2×HCID 58521874{[2-Fluoro-5-(propylsulfonyl)phenyl]ethynyl}trimethyl silane

Product 1

HCID 58522074Tert-butyl(4-chloro-2-{[4-fluoro-2-methyl-5-(methylsulfonyl)phenyl]ethynyl}phenoxy)acetate

Procedure

Following the general method as outlined in Intermediate 107, starting from (4-chloro-2-ethynyl-phenoxy)-acetic acid tert-butyl ester (Intermediate 3) and 1-bromo-4-fluoro-5-methanesulfonyl-2-methyl-benzene (Ger. Offen. 2000; DE 19919349), the title compound was obtained as a brown oil after purification by flash column chromatography (silica), eluting with cyclohexane containing increasing amounts of EtOAc.

Sources & evidence

ORD record
ord-f85a2046f8ef4862893fad11c5f2c6c5
Source dataset
uspto-grants-2012_09
Patent number
US08273769B2

Reaction notes

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