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

HRID 2390167Notes

Reaction equation

HRID 2390167 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].[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([S:26]([CH3:29])(=[O:28])=[O:27])=[CH:22][C:21]=1I>>[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:21]1[CH:22]=[C:23]([S:26]([CH3:29])(=[O:27])=[O:28])[CH:24]=[CH:25][C:20]=1[Cl:19])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 56594381Tert-butyl(4-chloro-2-ethynylphenoxy)acetate2×HCID 585220781-Chloro-2-iodo-4-(methylsulfonyl)benzene2×

Product 1

HCID 58521905Tert-butyl(4-chloro-2-{[2-chloro-5-(methylsulfonyl)phenyl]ethynyl}phenoxy)acetate

Procedure

Following the general method as outlined in Intermediate 79, starting from (4-chloro-2-ethynyl-phenoxy)-acetic acid tert-butyl ester (Intermediate 3) and 1-chloro-2-iodo-4-(methylsulfonyl)benzene (Intermediate 74), the title compound was obtained after purification by flash column chromatography (silica), eluting with cyclohexane containing increasing amounts of EtOAc.

Sources & evidence

ORD record
ord-b0c78e725812437f90c21ed728843c04
Source dataset
uspto-grants-2012_09
Patent number
US08273769B2

Reaction notes

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