Tert-butyl(3-chloro-2-iodophenoxy)acetate → Tert-butyl(3-chloro-2-{[3-(propylsulfonyl)phenyl]ethynyl}phenoxy)acetate

HRID 2390180Notes

Reaction equation

HRID 2390180 reaction equation
[C:1]([O:5][C:6](=[O:17])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[C:10]=1I)([CH3:4])([CH3:3])[CH3:2].[C:18]([C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([S:26]([CH2:29][CH2:30][CH3:31])(=[O:28])=[O:27])[CH:21]=1)#[CH:19]>>[C:1]([O:5][C:6](=[O:17])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[C:10]=1[C:19]#[C:18][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([S:26]([CH2:29][CH2:30][CH3:31])(=[O:28])=[O:27])[CH:21]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 16741488Tert-butyl(3-chloro-2-iodophenoxy)acetate2×HCID 565942671-Ethynyl-3-(propylsulfonyl)benzene2×

Product 1

HCID 58522089Tert-butyl(3-chloro-2-{[3-(propylsulfonyl)phenyl]ethynyl}phenoxy)acetate

Procedure

Following the general method as outlined in Intermediate 79, starting from (3-chloro-2-iodo-phenoxy)-acetic acid tert-butyl ester (Intermediate 94) and 1-ethynyl-3-(propane-1-sulfonyl)-benzene (Intermediate 42), the title compound was obtained a brown sticky solid after purification by flash column chromatography (silica), eluting with cyclohexane containing increasing amounts of EtOAc.

Sources & evidence

ORD record
ord-7240c644d3b54d58bd829093603d2bc5
Source dataset
uspto-grants-2012_09
Patent number
US08273769B2

Reaction notes

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