Tert-butyl(4-chloro-2-ethynylphenoxy)acetate → HCID 58522061, compound

HRID 2390213Notes

Reaction equation

HRID 2390213 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]([CH2:48][CH:49]([CH3:51])[CH3:50])(=[O:47])=[O:46])[CH:42]=[CH:41][C:40]=1[F: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:41]1[CH:42]=[C:43]([S:45]([CH2:48][CH:49]([CH3:50])[CH3:51])(=[O:46])=[O:47])[CH:44]=[CH:39][C:40]=1[F:52])([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 58522058HCID 58522058, compound2×

Product 1

HCID 58522061HCID 58522061, compoundYield 99%

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 2-Bromo-1-fluoro-4-(2-methyl-propane-1-sulfonyl)-benzene (Intermediate 131), the title compound was obtained as a colorless oil in 99% yield after purification by flash column chromatography (silica), eluting with cyclohexane containing increasing amounts of EtOAc.

Sources & evidence

ORD record
ord-a5c6a5c9d35a4afcb6058baf8ad60bd3
Source dataset
uspto-grants-2012_09
Patent number
US08273769B2

Reaction notes

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