1-(4-Difluoromethoxy-3-methyl-phenyl)-ethanone → (RS)-1-(3-bromo-5-ethoxymethyl-phenyl)-1-(4-difluoromethoxy-3-methyl-phenyl)-ethanol

HRID 1668748Notes

Reaction equation

HRID 1668748 reaction equation
[F:1][CH:2]([F:14])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:12])[CH3:11])=[CH:6][C:5]=1[CH3:13].Br[C:16]1[CH:21]=[C:20]([CH2:22][O:23][CH2:24][CH3:25])[CH:19]=[C:18]([Br:26])[CH:17]=1.C([Li])CCC>>[Br:26][C:18]1[CH:17]=[C:16]([C:10]([C:7]2[CH:8]=[CH:9][C:4]([O:3][CH:2]([F:1])[F:14])=[C:5]([CH3:13])[CH:6]=2)([OH:12])[CH3:11])[CH:21]=[C:20]([CH2:22][O:23][CH2:24][CH3:25])[CH:19]=1

Participants

4

Reactant 3

HCID 141529501-(4-Difluoromethoxy-3-methyl-phenyl)-ethanoneHCID 578250901,3-Dibromo-5-ethoxymethyl-benzeneHCID 178418339Butyllithium

Product 1

HCID 67347572(RS)-1-(3-bromo-5-ethoxymethyl-phenyl)-1-(4-difluoromethoxy-3-methyl-phenyl)-ethanol

Procedure

In an analogous reaction sequence to that described for Building Block C, the treatment of 1-(4-difluoromethoxy-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-difluoromethoxy-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: 47% of theory) as a light yellow oil. Mass (calculated) C19H19BrF2O2 [396]; (found) [M]+=396, 398.

Sources & evidence

ORD record
ord-f3ee6e17aca84669a0e035b4da6a03cd
Source dataset
uspto-grants-2011_08
Patent number
US07989449B2

Reaction notes

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