Tert-butyl(4-chloro-2-ethynylphenoxy)acetate → HCID 58521966, compound

HRID 2390212Notes

Reaction equation

HRID 2390212 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH2:11][CH2:12]C)(=[O:10])=[O:9])=[CH:4][C:3]=1[C:14]#[C:15][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]=1C#C)([CH3:23])([CH3:22])[CH3:21].BrC1C=C(S(CC)(=O)=O)C=CC=1F>>[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:15]#[C:14][C:3]1[CH:4]=[C:5]([S:8]([CH2:11][CH3:12])(=[O:10])=[O:9])[CH:6]=[CH:7][C:2]=1[F:1])([CH3:23])([CH3:21])[CH3:22]

Participants

4

Reactant 3

HCID 56594381Tert-butyl(4-chloro-2-ethynylphenoxy)acetate2×HCID 58521874{[2-Fluoro-5-(propylsulfonyl)phenyl]ethynyl}trimethyl silaneHCID 585219752-Bromo-4-(ethylsulfonyl)-1-fluorobenzene2×

Product 1

HCID 58521966HCID 58521966, compoundYield 86%

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-4-ethanesulfonyl-1-fluoro-benzene (Intermediate 130), the title compound was obtained as a colorless oil in 86% yield after purification by flash column chromatography (silica), eluting with cyclohexane containing increasing amounts of EtOAc.

Sources & evidence

ORD record
ord-0c3c33bebb064aaabd8394b6d4f9b48a
Source dataset
uspto-grants-2012_09
Patent number
US08273769B2

Reaction notes

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