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

HRID 888658Notes

Reaction equation

HRID 888658 reaction equation
[CH3:1][O:2][C:3](=[O:31])[CH:4]([C:9]1[CH:14]=[C:13]([O:15][S:16]([C:19]([F:22])([F:21])[F:20])(=[O:18])=[O:17])[CH:12]=[C:11](OCC2C=CC=CC=2)[CH:10]=1)[CH2:5][C:6]([CH3:8])=[CH2:7].[Cl:32][C:33]1[C:38]([C:39]([F:42])([F:41])[F:40])=[CH:37][C:36](B(O)O)=[CH:35][CH:34]=1>>[CH3:1][O:2][C:3](=[O:31])[CH:4]([C:9]1[CH:10]=[C:11]([C:36]2[CH:35]=[CH:34][C:33]([Cl:32])=[C:38]([C:39]([F:42])([F:41])[F:40])[CH:37]=2)[CH:12]=[C:13]([O:15][S:16]([C:19]([F:22])([F:20])[F:21])(=[O:17])=[O:18])[CH:14]=1)[CH2:5][CH:6]([CH3:7])[CH3:8]

Participants

3

Reactant 2

HCID 27826714-Chloro-3-(trifluoromethyl)benzeneboronic acidHCID 577550372-(3-Benzyloxy-5-trifluoromethanesulfonyloxy-phenyl)-4-methyl-pent-4-enoic acid methyl ester

Product 1

HCID 577549642-(4'-Chloro-5-trifluoromethanesulfonyloxy-3'-trifluoromethyl-biphenyl-3-yl)-4-methyl-pentanoic acid methyl esterYield 70%

Procedure

The title compound was prepared in 70% yield from 2-(3-benzyloxy-5-trifluoromethanesulfonyloxy-phenyl)-4-methyl-pent-4-enoic acid methyl ester (prepared in Example 1, step (d)) under the conditions described in Example 1, step (e-g)) using 4-chloro-5-trifluoromethylphenylboronic acid in step (e). RT=4.31 min

Sources & evidence

ORD record
ord-a9f198cd191e4bc49f269b594d351f41
Source dataset
uspto-grants-2012_08
Patent number
US08247610B2

Reaction notes

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