6-Bromo-2,2,3-trimethyl-1,1-dioxido-2,3-dihydro-1-benzothien-3-yl methyl ether → Tert-butyl{4-chloro-2-[(3-methoxy-2,2,3-trimethyl-1,1-dioxido-2,3-dihydro-1-benzothien-6-yl)ethynyl]phenoxy}acetate

HRID 2390301Notes

Reaction equation

HRID 2390301 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].[CH3:38][O:39][C:40]1([CH3:54])[C:44]2[CH:45]=[CH:46][C:47](Br)=[CH:48][C:43]=2[S:42](=[O:51])(=[O:50])[C:41]1([CH3:53])[CH3:52]>>[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:47]1[CH:46]=[CH:45][C:44]2[C:40]([O:39][CH3:38])([CH3:54])[C:41]([CH3:53])([CH3:52])[S:42](=[O:50])(=[O:51])[C:43]=2[CH:48]=1)([CH3:23])([CH3:22])[CH3:21]

Participants

4

Reactant 3

HCID 565941146-Bromo-2,2,3-trimethyl-1,1-dioxido-2,3-dihydro-1-benzothien-3-yl methyl ether2×HCID 56594381Tert-butyl(4-chloro-2-ethynylphenoxy)acetate2×HCID 58521874{[2-Fluoro-5-(propylsulfonyl)phenyl]ethynyl}trimethyl silane

Product 1

HCID 58522093Tert-butyl{4-chloro-2-[(3-methoxy-2,2,3-trimethyl-1,1-dioxido-2,3-dihydro-1-benzothien-6-yl)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 6-bromo-2,2,3-trimethyl-1,1-dioxido-2,3-dihydro-1-benzothien-3-yl methyl ether (Intermediate 250), the title compound was obtained after purification by flash column chromatography (silica), eluting with cyclohexane containing increasing amounts of EtOAc.

Sources & evidence

ORD record
ord-9e64f3b32dec408a85a7331230a500db
Source dataset
uspto-grants-2012_09
Patent number
US08273769B2

Reaction notes

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