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

HRID 2390158Notes

Reaction equation

HRID 2390158 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].I[C:20]1[CH:25]=[C:24]([S:26]([CH3:29])(=[O:28])=[O:27])[CH:23]=[CH:22][C:21]=1[CH2:30][CH2:31][CH3:32]>>[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:26]([CH3:29])(=[O:27])=[O:28])[CH:25]=[CH:20][C:21]=1[CH2:30][CH2:31][CH3:32])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 56594381Tert-butyl(4-chloro-2-ethynylphenoxy)acetate2×HCID 585220032-Iodo-4-(methylsulfonyl)-1-propylbenzene2×

Product 1

HCID 58522017Tert-butyl 2-[4-chloro-2-[2-(5-methylsulfonyl-2-propylphenyl)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 2-iodo-4-(methylsulfonyl)-1-propylbenzene (Intermediate 62), the title compound was obtained as a white solid after purification by flash column chromatography (silica), eluting with cyclohexane containing increasing amounts of EtOAc

Sources & evidence

ORD record
ord-9c731b6ba9174466aee38030f16a4a28
Source dataset
uspto-grants-2012_09
Patent number
US08273769B2

Reaction notes

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