3-Fluoro-5-(trifluoromethyl)benzeneboronic acid → 2-(3'-Fluoro-5-hydroxy-5'-trifluoromethyl-biphenyl-3-yl)-4-methyl-pentanoic acid methyl ester

HRID 226516Notes

Reaction equation

HRID 226516 reaction equation
[CH3:1][O:2][C:3](=[O:31])[CH:4]([C:9]1[CH:14]=[C:13]([O:15]S(C(F)(F)F)(=O)=O)[CH:12]=[C:11](OCC2C=CC=CC=2)[CH:10]=1)[CH2:5][C:6]([CH3:8])=[CH2:7].[F:32][C:33]1[CH:34]=[C:35](B(O)O)[CH:36]=[C:37]([C:39]([F:42])([F:41])[F:40])[CH:38]=1>>[CH3:1][O:2][C:3](=[O:31])[CH:4]([C:9]1[CH:10]=[C:11]([C:35]2[CH:36]=[C:37]([C:39]([F:41])([F:40])[F:42])[CH:38]=[C:33]([F:32])[CH:34]=2)[CH:12]=[C:13]([OH:15])[CH:14]=1)[CH2:5][CH:6]([CH3:7])[CH3:8]

Participants

3

Reactant 2

HCID 27831923-Fluoro-5-(trifluoromethyl)benzeneboronic acidHCID 577550372-(3-Benzyloxy-5-trifluoromethanesulfonyloxy-phenyl)-4-methyl-pent-4-enoic acid methyl ester

Product 1

HCID 577550352-(3'-Fluoro-5-hydroxy-5'-trifluoromethyl-biphenyl-3-yl)-4-methyl-pentanoic acid methyl esterYield 73%

Procedure

The title compound was prepared in 73% yield from 2-(3-benzyloxy-5-trifluoromethanesulfonyloxy-phenyl)-4-methyl-pent-4-enoic acid methyl ester (prepared in Example 15, step (d)) under the conditions described in Example 15, step (e-f) using 3-fluoro-5-trifluoromethylphenylboronic acid in step (e).

Sources & evidence

ORD record
ord-4db8c7698c2a438583a62357213a7983
Source dataset
uspto-grants-2009_07
Patent number
US07557244B2

Reaction notes

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