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

HRID 1482087Notes

Reaction equation

HRID 1482087 reaction equation
Br[C:2]1[CH:7]=[C:6]([O:8][C:9]([F:12])([F:11])[F:10])[CH:5]=[CH:4][C:3]=1[O:13][C@H:14]([CH2:16][CH:17]=[CH2:18])[CH3:15].FC1C(F)=CC([B:27]2[O:34][C:33](=[O:35])[CH2:32][N:31]([CH3:36])[CH2:30][C:29](=[O:37])[O:28]2)=C(O[C@H](CC=C)C)C=1>>[CH3:36][N:31]1[CH2:32][C:33](=[O:35])[O:34][B:27]([C:2]2[CH:7]=[C:6]([O:8][C:9]([F:12])([F:11])[F:10])[CH:5]=[CH:4][C:3]=2[O:13][C@H:14]([CH2:16][CH:17]=[CH2:18])[CH3:15])[O:28][C:29](=[O:37])[CH2:30]1

Participants

3

Reactant 2

HCID 118308885(S)-2-Bromo-1-(pent-4-en-2-yloxy)-4-(trifluoromethoxy)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 131736669(S)-6-Methyl-2-(2-(pent-4-en-2-yloxy)-5-(trifluoromethoxy)phenyl)-1,3,6,2-dioxazaborocane-4,8-dioneYield 68%

Procedure

Prepared in 68% yield from (S)-2-bromo-1-(pent-4-en-2-yloxy)-4-(trifluoromethoxy)benzene 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, CDCl3) δ 7.57 (d, J=3.0 Hz, 1H), 7.23 (dd, J=8.8, 3.0 Hz, 1H), 6.93 (d, J=8.8 Hz, 1H), 5.90-5.77 (m, 1H), 5.19-5.11 (m, 2H), 4.69-4.60 (m, 1H), 4.12 (d, J=16.1 Hz, 1H), 4.01-3.85 (m, 3H), 2.71 (s, 3H), 2.53 (dt, J=14.4, 7.1 Hz, 1H), 2.44-2.34 (m, 1H), 1.32 (d, J=6.0 Hz, 3H); 19F NMR (376 MHz, CDCl3) δ −58.20 (s, 3F).

Sources & evidence

ORD record
ord-fc68577fe6b9460b9bf55ef7d814fc3c
Source dataset
uspto-grants-2016_08
Patent number
US09409922B2

Reaction notes

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