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

HRID 1482014Notes

Reaction equation

HRID 1482014 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[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[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1[O:10][C@H:17]([CH2:12][CH:13]=[CH2:14])[CH3:16]

Participants

3

Reactant 2

HCID 27362882-Bromo-4,5-difluorophenolHCID 118308842(S)-1-Bromo-4-fluoro-2-(pent-4-en-2-yloxy)benzene

Product 1

HCID 118308806(S)-1-Bromo-4,5-difluoro-2-(pent-4-en-2-yloxy)benzeneYield 61%

Procedure

Prepared in 61% yield from 2-bromo-4,5-difluorophenol following the same procedure as (S)-1-bromo-4-fluoro-2-(pent-4-en-2-yloxy)benzene. 1H NMR (400 MHz, CDCl3) δ 7.42-7.35 (m, 1H), 6.77 (dd, J=11.9, 7.2 Hz, 1H), 5.88 (ddt, J=17.2, 10.1, 7.1 Hz, 1H), 5.21-5.06 (m, 2H), 4.40-4.27 (m, 1H), 2.61-2.36 (m, 2H), 1.35 (d, J=6.0 Hz, 3H).

Sources & evidence

ORD record
ord-e2cc3ce5b5104401a1f1951623576586
Source dataset
uspto-grants-2016_08
Patent number
US09409922B2

Reaction notes

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