2-Iodo-1-methyl-4-(phenylsulfonyl)benzene → Tert-butyl 2-[2-[2-[5-(benzenesulfonyl)-2-methylphenyl]ethynyl]-4-chlorophenoxy]acetate

HRID 2390199Notes

Reaction equation

HRID 2390199 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]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)(=[O:28])=[O:27])[CH:23]=[CH:22][C:21]=1[CH3:35]>>[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]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)(=[O:28])=[O:27])[CH:25]=[CH:20][C:21]=1[CH3:35])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 565939772-Iodo-1-methyl-4-(phenylsulfonyl)benzene2×HCID 56594381Tert-butyl(4-chloro-2-ethynylphenoxy)acetate2×

Product 1

HCID 58522004Tert-butyl 2-[2-[2-[5-(benzenesulfonyl)-2-methylphenyl]ethynyl]-4-chlorophenoxy]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-1-methyl-4-(phenylsulfonyl)benzene (Intermediate 114), the title compound was obtained as a brown sticky solid in quantitative yield after purification by flash column chromatography (silica), eluting with cyclohexane containing increasing amounts of EtOAc.

Sources & evidence

ORD record
ord-01423c14004046239960410c6293b89e
Source dataset
uspto-grants-2012_09
Patent number
US08273769B2

Reaction notes

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