(S)-1-bromo-3,5-difluoro-2-(pent-4-en-2-yloxy)benzene → (S)-2-(3,5-Difluoro-2-(pent-4-en-2-yloxy)phenyl)-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione

HRID 1482099Notes

Reaction equation

HRID 1482099 reaction equation
Br[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([F:9])[C:3]=1[O:10][C@H:11]([CH2:13][CH:14]=[CH2:15])[CH3:12].FC1C(F)=CC([B:24]2[O:31][C:30](=[O:32])[CH2:29][N:28]([CH3:33])[CH2:27][C:26](=[O:34])[O:25]2)=C(O[C@H](CC=C)C)C=1>>[F:9][C:4]1[C:3]([O:10][C@H:11]([CH2:13][CH:14]=[CH2:15])[CH3:12])=[C:2]([B:24]2[O:31][C:30](=[O:32])[CH2:29][N:28]([CH3:33])[CH2:27][C:26](=[O:34])[O:25]2)[CH:7]=[C:6]([F:8])[CH:5]=1

Participants

3

Reactant 2

HCID 118308830(S)-1-bromo-3,5-difluoro-2-(pent-4-en-2-yloxy)benzeneHCID 131736668(S)-2-(4,5-difluoro-2-(pent-4-en-2-yloxy)phenyl)-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione

Product 1

HCID 131736671(S)-2-(3,5-Difluoro-2-(pent-4-en-2-yloxy)phenyl)-6-methyl-1,3,6,2-dioxazaborocane-4,8-dioneYield 40%

Procedure

Prepared from (S)-1-bromo-3,5-difluoro-2-(pent-4-en-2-yloxy)benzene in 40% yield following the procedure for (S)-2-(4,5-difluoro-2-(pent-4-en-2-yloxy)phenyl)-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione. 1H NMR (400 MHz, CDCl3) δ 7.21 (dd, J=8.5, 1.8 Hz, 1H), 6.89 (ddd, J=12.5, 7.8, 3.3 Hz, 1H), 5.91-5.73 (m, 1H), 5.17-5.03 (m, 2H), 4.88-4.75 (m, 1H), 4.10-3.95 (m, 1H), 3.92-3.83 (m, 3H), 2.66 (s, 3H), 2.53-2.41 (m, 1H), 2.39-2.28 (m, 1H), 1.24 (d, J=6.3 Hz, 3H); 19F NMR (376 MHz, CDCl3) δ −117.18 (d, J=5.2 Hz, 1F), −122.14 (d, J=5.2 Hz, 1F).

Sources & evidence

ORD record
ord-25854fbc8cd64280bd533b6b90ddd3d9
Source dataset
uspto-grants-2016_08
Patent number
US09409922B2

Reaction notes

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