Tert-butyl(4-chloro-2-ethynylphenoxy)acetate → HCID 58521960, compound

HRID 2390270Notes

Reaction equation

HRID 2390270 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]=[CH:43][C:42]([C:45]2[CH:50]=[CH:49][CH:48]=[C:47]([Cl:51])[CH:46]=2)=[C:41]([S:52]([CH3:55])(=[O:54])=[O:53])[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:44]=[CH:43][C:42]([C:45]2[CH:50]=[CH:49][CH:48]=[C:47]([Cl:51])[CH:46]=2)=[C:41]([S:52]([CH3:55])(=[O:53])=[O:54])[CH:40]=1)([CH3:23])([CH3:22])[CH3:21]

Participants

4

Reactant 3

HCID 56594381Tert-butyl(4-chloro-2-ethynylphenoxy)acetate2×HCID 58521831HCID 58521831, compound2×HCID 58521874{[2-Fluoro-5-(propylsulfonyl)phenyl]ethynyl}trimethyl silane

Product 1

HCID 58521960HCID 58521960, compound

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 4-bromo-3′-chloro-2-(methylsulfonyl)biphenyl (Intermediate 213), the title compound was obtained as a brown sticky solid after purification by flash column chromatography (silica), eluting with cyclohexane containing increasing amounts of EtOAc.

Sources & evidence

ORD record
ord-7a8bca9382114af088f2f4b1ce86c9cd
Source dataset
uspto-grants-2012_09
Patent number
US08273769B2

Reaction notes

Loading…