3,4-Difluorophenol → (S)-1,2-Difluoro-4-(pent-4-en-2-yloxy)benzene

HRID 1482104Notes

Reaction equation

HRID 1482104 reaction equation
FC1C=C(O)C=CC=1F.[F:10][C:11]1[C:16]([F:17])=[CH:15][C:14](B2OC(=O)CN(C)CC(=O)O2)=[C:13]([O:29][C@H:30]([CH2:32][CH:33]=[CH2:34])[CH3:31])[CH:12]=1>>[F:17][C:16]1[CH:15]=[CH:14][C:13]([O:29][C@H:30]([CH2:32][CH:33]=[CH2:34])[CH3:31])=[CH:12][C:11]=1[F:10]

Participants

3

Reactant 2

HCID 759273,4-DifluorophenolHCID 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 118308803(S)-1,2-Difluoro-4-(pent-4-en-2-yloxy)benzene

Procedure

Prepared in 69% from 3,4-difluorophenol 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 7.11-6.97 (m, 1H), 6.72 (ddd, J=12.1, 6.6, 2.9 Hz, 1H), 6.64-6.54 (m, 1H), 5.85 (ddt, J=17.2, 10.2, 7.0 Hz, 1H), 5.19-5.09 (m, 2H), 4.38-4.23 (m, 1H), 2.48 (qd, J=7.0, 5.9 Hz, 1H), 2.40-2.28 (m, 1H), 1.31 (d, J=6.0 Hz, 3H); 19F NMR (376 MHz, CDCl3) δ −135.75 (d, J=20.8 Hz, 1F), −148.32 (d, J=22.5 Hz, 1F).

Sources & evidence

ORD record
ord-f04b0a03cf2e4b2aa371abc44261c110
Source dataset
uspto-grants-2016_08
Patent number
US09409922B2

Reaction notes

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