2-Bromo-3,5-difluorophenol → (S)-2-Bromo-1,5-difluoro-3-(pent-4-en-2-yloxy)benzene

HRID 1482091Notes

Reaction equation

HRID 1482091 reaction equation
[Br:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([F:9])=[CH:4][C:3]=1[OH:10].F[C:12]1[C:17](F)=[CH:16]C(B2OC(=O)CN(C)CC(=O)O2)=[C:14](O[C@H](CC=C)C)[CH:13]=1>>[Br:1][C:2]1[C:3]([O:10][C@H:17]([CH2:12][CH:13]=[CH2:14])[CH3:16])=[CH:4][C:5]([F:9])=[CH:6][C:7]=1[F:8]

Participants

3

Reactant 2

HCID 221448602-Bromo-3,5-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 118308799(S)-2-Bromo-1,5-difluoro-3-(pent-4-en-2-yloxy)benzeneYield 80%

Procedure

Prepared from 2-bromo-3,5-difluorophenol in 80% 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 6.59-6.43 (m, 2H), 5.94-5.80 (m, 1H), 5.22-5.09 (m, 2H), 4.47-4.36 (m, 1H), 2.59-2.37 (m, 2H), 1.37 (d, J=6.3 Hz, 3H).

Sources & evidence

ORD record
ord-32f2c6a027cf4c95b0fc734ce1f2fdc8
Source dataset
uspto-grants-2016_08
Patent number
US09409922B2

Reaction notes

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