2-Bromo-1-methyl-4-(propylsulfinyl)benzene → Methyl (4-chloro-2-{[2-methyl-5-(propylsulfinyl)phenyl]ethynyl}phenoxy)acetate

HRID 2390276Notes

Reaction equation

HRID 2390276 reaction equation
FC1C=CC(S(CCC)(=O)=O)=CC=1C#C[Si](C)(C)C.[Cl:20][C:21]1[CH:32]=[CH:31][C:24]([O:25][CH2:26][C:27]([O:29][CH3:30])=[O:28])=[C:23]([C:33]#[CH:34])[CH:22]=1.Br[C:36]1[CH:41]=[C:40]([S:42]([CH2:44][CH2:45][CH3:46])=[O:43])[CH:39]=[CH:38][C:37]=1[CH3:47]>>[Cl:20][C:21]1[CH:32]=[CH:31][C:24]([O:25][CH2:26][C:27]([O:29][CH3:30])=[O:28])=[C:23]([C:33]#[C:34][C:36]2[CH:41]=[C:40]([S:42]([CH2:44][CH2:45][CH3:46])=[O:43])[CH:39]=[CH:38][C:37]=2[CH3:47])[CH:22]=1

Participants

4

Reactant 3

HCID 565939782-Bromo-1-methyl-4-(propylsulfinyl)benzene2×HCID 58521874{[2-Fluoro-5-(propylsulfonyl)phenyl]ethynyl}trimethyl silaneHCID 58522019Methyl (4-chloro-2-ethynylphenoxy)acetate2×

Product 1

HCID 56593979Methyl (4-chloro-2-{[2-methyl-5-(propylsulfinyl)phenyl]ethynyl}phenoxy)acetate

Procedure

Following the general method as outlined in Intermediate 107, starting from methyl (4-chloro-2-ethynylphenoxy)acetate (Intermediate 220) and 2-bromo-1-methyl-4-(propylsulfinyl)benzene (Intermediate 219), the title compound was obtained as a yellow oil after purification by flash column chromatography (silica), eluting with cyclohexane containing increasing amounts of EtOAc.

Sources & evidence

ORD record
ord-77ae0bb8a5f542079e1600e837e090e2
Source dataset
uspto-grants-2012_09
Patent number
US08273769B2

Reaction notes

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