1-(4-Methoxy-3-methylphenyl)ethan-1-one → (RS)-1-(3-bromo-5-ethoxymethyl-phenyl)-1-(4-methoxy-3-methyl-phenyl)-ethanol

HRID 1668749Notes

Reaction equation

HRID 1668749 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:11])[CH3:10])=[CH:5][C:4]=1[CH3:12].Br[C:14]1[CH:19]=[C:18]([CH2:20][O:21][CH2:22][CH3:23])[CH:17]=[C:16]([Br:24])[CH:15]=1.C([Li])CCC>>[Br:24][C:16]1[CH:15]=[C:14]([C:9]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[C:4]([CH3:12])[CH:5]=2)([OH:11])[CH3:10])[CH:19]=[C:18]([CH2:20][O:21][CH2:22][CH3:23])[CH:17]=1

Participants

4

Reactant 3

HCID 248061-(4-Methoxy-3-methylphenyl)ethan-1-oneHCID 578250901,3-Dibromo-5-ethoxymethyl-benzeneHCID 178418339Butyllithium

Product 1

HCID 67348902(RS)-1-(3-bromo-5-ethoxymethyl-phenyl)-1-(4-methoxy-3-methyl-phenyl)-ethanol

Procedure

In an analogous reaction sequence to that described for Building Block C, the treatment of 1-(4-methoxy-3-methyl-phenyl)-ethanone with 1,3-dibromo-5-ethoxymethyl-benzene beforehand reacted with n-butyllithium, yielded the (RS)-1-(3-bromo-5-ethoxymethyl-phenyl)-1-(4-methoxy-3-methyl-phenyl)-ethanol which was used as crude material in the following elimination reaction with a catalytic amount of p-toluenesulfonic acid to yield the title compound (yield: 86% of theory) as a colourless oil. Mass (calculated) C19H21BrO2 [360]; (found) [M+H]+=361, 363.

Sources & evidence

ORD record
ord-6feaf03c92694796a16e549bd262e429
Source dataset
uspto-grants-2011_08
Patent number
US07989449B2

Reaction notes

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