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

Participants

Role	Name	HCID	Charge
Reactant	3,4-Difluorophenol	HCID 75927	—
Reactant	(S)-2-(4,5-difluoro-2-(pent-4-en-2-yloxy)phenyl)-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione	HCID 131736668	—
Product	(S)-1,2-Difluoro-4-(pent-4-en-2-yloxy)benzene	HCID 118308803	—

Reaction Steps

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).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09409922B2
Source dataset	uspto-grants-2016_08
ORD ID	ord-f04b0a03cf2e4b2aa371abc44261c110
Source note	uspto-grants-2016_08