2-Bromo-4,6-difluorophenol → (S)-1-bromo-3,5-difluoro-2-(pent-4-en-2-yloxy)benzene

HRID 1482098Notes

Reaction equation

HRID 1482098 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([F:9])[C:3]=1[OH:10].Br[C:12]1[CH:17]=[C:16](F)C(F)=[CH:14][C:13]=1O[C@H](CC=C)C>>[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([F:9])[C:3]=1[O:10][C@H:17]([CH2:12][CH:13]=[CH2:14])[CH3:16]

Participants

3

Reactant 2

HCID 27362902-Bromo-4,6-difluorophenolHCID 118308806(S)-1-Bromo-4,5-difluoro-2-(pent-4-en-2-yloxy)benzene

Product 1

HCID 118308830(S)-1-bromo-3,5-difluoro-2-(pent-4-en-2-yloxy)benzeneYield 92%

Procedure

Prepared in 92% yield from 2-bromo-4,6-difluorophenol following the procedure for (S)-1-bromo-4,5-difluoro-2-(pent-4-en-2-yloxy)benzene. 1H NMR (400 MHz, CDCl3) δ 7.19-7.06 (m, 1H), 6.85 (ddd, J=10.9, 8.2, 3.0 Hz, 1H), 5.90 (ddt, J=17.2, 10.1, 7.0 Hz, 1H), 5.19-5.07 (m, 2H), 4.46-4.30 (m, 1H), 2.65-2.48 (m, 1H), 2.48-2.39 (m, 1H), 1.31 (dd, J=6.1, 0.6 Hz, 3H).

Sources & evidence

ORD record
ord-5e6631952be94fd3b44bf09265fcbef3
Source dataset
uspto-grants-2016_08
Patent number
US09409922B2

Reaction notes

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