Tert-butyl(4-chloro-2-ethynylphenoxy)acetate → HCID 58522075, compound

HRID 2390305Notes

Reaction equation

HRID 2390305 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:49]=[CH:48][C:42]([C:43]([N:45]([CH3:47])[CH3:46])=[O:44])=[C:41]([S:50]([CH:53]([CH3:55])[CH3:54])(=[O:52])=[O:51])[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:49]=[CH:48][C:42]([C:43]([N:45]([CH3:46])[CH3:47])=[O:44])=[C:41]([S:50]([CH:53]([CH3:55])[CH3:54])(=[O:51])=[O:52])[CH:40]=1)([CH3:23])([CH3:22])[CH3:21]

Participants

4

Reactant 3

HCID 56594381Tert-butyl(4-chloro-2-ethynylphenoxy)acetate2×HCID 58521874{[2-Fluoro-5-(propylsulfonyl)phenyl]ethynyl}trimethyl silaneHCID 58522027HCID 58522027, compound2×

Product 1

HCID 58522075HCID 58522075, 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-2-(isopropylsulfonyl)-N,N-dimethylbenzamide (Intermediate 255), the title compound was obtained as brown sticky solid after purification by flash column chromatography (silica), eluting with cyclohexane containing increasing amounts of EtOAc.

Sources & evidence

ORD record
ord-c2f70a32331e4921817c94560ceb99ab
Source dataset
uspto-grants-2012_09
Patent number
US08273769B2

Reaction notes

Loading…