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

HRID 1482092Notes

Reaction equation

HRID 1482092 reaction equation
Br[C:2]1[C:7]([O:8][C@H:9]([CH2:11][CH:12]=[CH2:13])[CH3:10])=[CH:6][C:5]([F:14])=[CH:4][C:3]=1[F:15].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:15][C:3]1[CH:4]=[C:5]([F:14])[CH:6]=[C:7]([O:8][C@H:9]([CH2:11][CH:12]=[CH2:13])[CH3:10])[C:2]=1[B:24]1[O:31][C:30](=[O:32])[CH2:29][N:28]([CH3:33])[CH2:27][C:26](=[O:34])[O:25]1

Participants

3

Reactant 2

HCID 118308799(S)-2-Bromo-1,5-difluoro-3-(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 131736670(S)-2-(2,4-Difluoro-6-(pent-4-en-2-yloxy)phenyl)-6-methyl-1,3,6,2-dioxazaborocane-4,8-dioneYield 58%

Procedure

Prepared from (S)-2-bromo-1,5-difluoro-3-(pent-4-en-2-yloxy)benzene in 58% yield following the same procedure as (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, DMSO-d6) 6.84 (d, J=11.5 Hz, 1H), 6.67-6.59 (m, 1H), 5.89-5.78 (m, 1H), 5.16-5.02 (m, 2H), 4.71-4.60 (m, 1H), 4.35 (dd, J=17.2, 5.6 Hz, 2H), 4.05-3.92 (m, 2H), 2.65 (s, 3H), 2.46-2.36 (m, 1H), 2.25 (dt, J=14.3, 6.9 Hz, 1H), 1.17 (d, J=6.0 Hz, 3H).

Sources & evidence

ORD record
ord-7e71b3aa4ea247a59089183206165b26
Source dataset
uspto-grants-2016_08
Patent number
US09409922B2

Reaction notes

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