(S)-2-Bromo-4-fluoro-1-(pent-4-en-2-yloxy)benzene → (S)-(5-Fluoro-2-(pent-4-en-2-yloxy)phenyl)boronic acid

HRID 1482010Notes

Reaction equation

HRID 1482010 reaction equation
Br[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[O:9][C@H:10]([CH2:12][CH:13]=[CH2:14])[CH3:11].FC1C=CC([B:22]([OH:24])[OH:23])=C(O[C@H](CC=C)C)C=1>>[F:8][C:6]1[CH:5]=[CH:4][C:3]([O:9][C@H:10]([CH2:12][CH:13]=[CH2:14])[CH3:11])=[C:2]([B:22]([OH:24])[OH:23])[CH:7]=1

Participants

3

Reactant 2

HCID 118308863(S)-2-Bromo-4-fluoro-1-(pent-4-en-2-yloxy)benzeneHCID 123945833(S)-(4-Fluoro-2-(pent-4-en-2-yloxy)phenyl)boronic acid

Product 1

HCID 123488148(S)-(5-Fluoro-2-(pent-4-en-2-yloxy)phenyl)boronic acidYield 100%

Procedure

Prepared from (S)-2-bromo-4-fluoro-1-(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-485c7b1f5e8947a8a207d9cf2433724f
Source dataset
uspto-grants-2016_08
Patent number
US09409922B2

Reaction notes

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