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

HRID 1482019Notes

Reaction equation

HRID 1482019 reaction equation
[Br:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([F:9])=[CH:4][C:3]=1[OH:10].Br[C:12]1[CH:17]=[CH:16]C(F)=[CH:14][C:13]=1O[C@H](CC=C)C>>[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 118308842(S)-1-Bromo-4-fluoro-2-(pent-4-en-2-yloxy)benzene

Product 1

HCID 118308799(S)-2-Bromo-1,5-difluoro-3-(pent-4-en-2-yloxy)benzeneYield 75%

Procedure

Prepared in 75% yield from 2-bromo-3,5-difluorophenol following the same procedure as (S)-1-bromo-4-fluoro-2-(pent-4-en-2-yloxy)benzene. 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-1ab7901fa83d4fc18d62405853a8e1ec
Source dataset
uspto-grants-2016_08
Patent number
US09409922B2

Reaction notes

Loading…