6-bromo-2,2-dimethyl-1-benzothiophen-3(2H)-one 1,1-dioxide → Tert-butyl{4-chloro-2-[(2,2-dimethyl-1,1-dioxido-3-oxo-2,3-dihydro-1-benzothien-6-yl)ethynyl]phenoxy}acetate

HRID 2390293Notes

Reaction equation

HRID 2390293 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:52]=[CH:51][C:42]2[C:43](=[O:50])[C:44]([CH3:49])([CH3:48])[S:45](=[O:47])(=[O:46])[C:41]=2[CH:40]=1>>[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:52]=[CH:51][C:42]2[C:43](=[O:50])[C:44]([CH3:49])([CH3:48])[S:45](=[O:46])(=[O:47])[C:41]=2[CH:40]=1)([CH3:23])([CH3:22])[CH3:21]

Participants

4

Reactant 3

HCID 565941096-bromo-2,2-dimethyl-1-benzothiophen-3(2H)-one 1,1-dioxide2×HCID 56594381Tert-butyl(4-chloro-2-ethynylphenoxy)acetate2×HCID 58521874{[2-Fluoro-5-(propylsulfonyl)phenyl]ethynyl}trimethyl silane

Product 1

HCID 58521949Tert-butyl{4-chloro-2-[(2,2-dimethyl-1,1-dioxido-3-oxo-2,3-dihydro-1-benzothien-6-yl)ethynyl]phenoxy}acetateYield 91%

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 6-bromo-2,2-dimethyl-1-benzothiophen-3(2H)-one 1,1-dioxide (Intermediate 241), the title compound was obtained in 91% yield after purification by flash column chromatography (silica), eluting with cyclohexane containing increasing amounts of EtOAc.

Sources & evidence

ORD record
ord-475cdb6a90c9454db162156b7b75a46b
Source dataset
uspto-grants-2012_09
Patent number
US08273769B2

Reaction notes

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