2-Bromo-4-chloro-1-(methoxymethoxy)benzene → 3-{[5-Chloro-2-(methoxymethoxy)phenyl]ethynyl}-4-methylphenyl propyl sulfone

HRID 2390315Notes

Reaction equation

HRID 2390315 reaction equation
C(OC(=O)COC1C(Br)=CC(Cl)=CN=1)(C)(C)C.Br[C:19]1[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:20]=1[O:26][CH2:27][O:28][CH3:29].[C:30]([C:32]1[CH:37]=[C:36]([S:38]([CH2:41][CH2:42][CH3:43])(=[O:40])=[O:39])[CH:35]=[CH:34][C:33]=1[CH3:44])#[CH:31]>>[CH2:41]([S:38]([C:36]1[CH:35]=[CH:34][C:33]([CH3:44])=[C:32]([C:30]#[C:31][C:19]2[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:20]=2[O:26][CH2:27][O:28][CH3:29])[CH:37]=1)(=[O:39])=[O:40])[CH2:42][CH3:43]

Participants

4

Reactant 3

HCID 107059212-Bromo-4-chloro-1-(methoxymethoxy)benzene2×HCID 58521889Tert-butyl[(3-bromo-5-chloropyridin-2-yl)oxy]acetateHCID 585220332-Ethynyl-1-methyl-4-(propylsulfonyl) benzene2×

Product 1

HCID 585220943-{[5-Chloro-2-(methoxymethoxy)phenyl]ethynyl}-4-methylphenyl propyl sulfoneYield 70%

Procedure

Following the general method as outlined in Intermediate 183, starting from 2-bromo-4-chloro-1-(methoxymethoxy)benzene (Intermediate 265) and 2-ethynyl-1-methyl-4-(propane-1-sulfonyl)-benzene (Intermediate 40), the title compound was obtained as a white solid in 70% yield after purification by flash column chromatography (silica), eluting with cyclohexane containing increasing amounts of EtOAc.

Sources & evidence

ORD record
ord-703f9c735a434ab3bc5bd5cfe22e73ff
Source dataset
uspto-grants-2012_09
Patent number
US08273769B2

Reaction notes

Loading…