Tert-butyl(4-chloro-2-ethynylphenoxy)acetate → Tert-butyl(4-chloro-2-{[2-ethyl-5-(methylsulfonyl)phenyl]ethynyl}phenoxy)acetate

HRID 2390205Notes

Reaction equation

HRID 2390205 reaction equation
[C:1]([O:5][C:6](=[O:18])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=1[C:16]#[CH:17])([CH3:4])([CH3:3])[CH3:2].[CH2:19]([C:21]1[CH:26]=[CH:25][C:24]([S:27]([CH3:30])(=[O:29])=[O:28])=[CH:23][C:22]=1I)[CH3:20]>>[C:1]([O:5][C:6](=[O:18])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=1[C:16]#[C:17][C:22]1[CH:23]=[C:24]([S:27]([CH3:30])(=[O:28])=[O:29])[CH:25]=[CH:26][C:21]=1[CH2:19][CH3:20])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 56594381Tert-butyl(4-chloro-2-ethynylphenoxy)acetate2×HCID 585218301-Ethyl-2-iodo-4-(methylsulfonyl)benzene2×

Product 1

HCID 58521866Tert-butyl(4-chloro-2-{[2-ethyl-5-(methylsulfonyl)phenyl]ethynyl}phenoxy)acetate

Procedure

Following the general method as outlined in Intermediate 20, starting from (4-chloro-2-ethynyl-phenoxy)-acetic acid tert-butyl ester (Intermediate 3) and 1-ethyl-2-iodo-4-(methylsulfonyl)benzene (Intermediate 123), the title compound was obtained as an orange oil after purification by flash column chromatography (silica), eluting with cyclohexane containing increasing amounts of EtOAc.

Sources & evidence

ORD record
ord-b3a4da7aec4b4fe3a674e71bd73e3912
Source dataset
uspto-grants-2012_09
Patent number
US08273769B2

Reaction notes

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