2-Bromo-4-fluorophenol → (S)-2-Bromo-4-fluoro-1-(pent-4-en-2-yloxy)benzene

HRID 1482009Notes

Reaction equation

HRID 1482009 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[OH:9].Br[C:11]1[CH:16]=[CH:15]C(F)=[CH:13][C:12]=1O[C@H](CC=C)C>>[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[O:9][C@H:16]([CH2:11][CH:12]=[CH2:13])[CH3:15]

Participants

3

Reactant 2

HCID 6054722-Bromo-4-fluorophenolHCID 118308842(S)-1-Bromo-4-fluoro-2-(pent-4-en-2-yloxy)benzene

Product 1

HCID 118308863(S)-2-Bromo-4-fluoro-1-(pent-4-en-2-yloxy)benzeneYield 88%

Procedure

Prepared from 2-bromo-4-fluorophenol in 88% yield following the same procedure as (S)-1-bromo-4-fluoro-2-(pent-4-en-2-yloxy)benzene. 1H NMR (400 MHz, CDCl3) δ 7.39-7.33 (m, 1H), 7.30 (dd, J=8.0, 3.0 Hz, 1H), 7.01-6.94 (m, 1H), 6.91-6.85 (m, 1H), 5.90 (ddt, J=17.2, 10.2, 7.0 Hz, 1H), 5.20-5.10 (m, 2H), 4.36 (sxt, J=6.1 Hz, 1H), 2.58-2.49 (m, 1H), 2.45-2.36 (m, 1H), 1.34 (d, J=6.0 Hz, 3H).

Sources & evidence

ORD record
ord-94177c987586494cb3c40f138c3c6e75
Source dataset
uspto-grants-2016_08
Patent number
US09409922B2

Reaction notes

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