(S)-1-Bromo-4,5-difluoro-2-(pent-4-en-2-yloxy)benzene → (S)-(4,5-Difluoro-2-(pent-4-en-2-yloxy)phenyl)boronic acid

HRID 1482015Notes

Reaction equation

HRID 1482015 reaction equation
Br[C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1[O:10][C@H:11]([CH2:13][CH:14]=[CH2:15])[CH3:12].FC1C=CC([B:23]([OH:25])[OH:24])=C(O[C@H](CC=C)C)C=1>>[F:9][C:5]1[C:6]([F:8])=[CH:7][C:2]([B:23]([OH:25])[OH:24])=[C:3]([O:10][C@H:11]([CH2:13][CH:14]=[CH2:15])[CH3:12])[CH:4]=1

Participants

3

Reactant 2

HCID 118308806(S)-1-Bromo-4,5-difluoro-2-(pent-4-en-2-yloxy)benzeneHCID 123945833(S)-(4-Fluoro-2-(pent-4-en-2-yloxy)phenyl)boronic acid

Product 1

HCID 123993303(S)-(4,5-Difluoro-2-(pent-4-en-2-yloxy)phenyl)boronic acidYield 100%

Procedure

Prepared from (S)-1-bromo-4,5-difluoro-2-(pent-4-en-2-yloxy)benzene in 100% yield following the same procedure as (S)-(4-fluoro-2-(pent-4-en-2-yloxy)phenyl)boronic acid. NMR is complex and suggests an oligomeric mixture. The material, however, was used as is and was fully compentent for undergoing a Suzuki coupling.

Sources & evidence

ORD record
ord-44e033bce72042d0ab4e0625910f5b41
Source dataset
uspto-grants-2016_08
Patent number
US09409922B2

Reaction notes

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