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

HRID 1482028Notes

Reaction equation

HRID 1482028 reaction equation
Br[C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([CH3:9])=[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>>[CH3:9][C:5]1[C:6]([CH3:8])=[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 89971250(S)-1-Bromo-4,5-dimethyl-2-(pent-4-en-2-yloxy)benzeneHCID 123945833(S)-(4-Fluoro-2-(pent-4-en-2-yloxy)phenyl)boronic acid

Product 1

HCID 123664321(S)-(4,5-Dimethyl-2-(pent-4-en-2-yloxy)phenyl)boronic acidYield 85%

Procedure

Prepared in 85% yield from (S)-1-bromo-4,5-dimethyl-2-(pent-4-en-2-yloxy)benzene following the procedure for (S)-(4-fluoro-2-(pent-4-en-2-yloxy)phenyl)boronic acid. 1H NMR (400 MHz, CDCl3) δ 7.57 (s, 1H), 6.72 (s, 1H), 5.93-5.82 (m, 1H), 5.81 (d, J=5.8 Hz, 2H), 5.22-5.13 (m, 2H), 4.68-4.55 (m, 1H), 2.60-2.42 (m, 2H), 2.28 (s, 3H), 2.22 (s, 3H), 1.38 (d, J=6.3 Hz, 3H).

Sources & evidence

ORD record
ord-6ad803d9ede34465983e6a15be8adcf0
Source dataset
uspto-grants-2016_08
Patent number
US09409922B2

Reaction notes

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