2-Bromo-4-fluoro-5-methylphenol → (S)-1-Bromo-5-fluoro-4-methyl-2-(pent-4-en-2-yloxy)benzene

HRID 1482035Notes

Reaction equation

HRID 1482035 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([CH3:9])=[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]([CH3:9])=[CH:4][C:3]=1[O:10][C@H:17]([CH2:12][CH:13]=[CH2:14])[CH3:16]

Participants

3

Reactant 2

HCID 846728312-Bromo-4-fluoro-5-methylphenolHCID 118308842(S)-1-Bromo-4-fluoro-2-(pent-4-en-2-yloxy)benzene

Product 1

HCID 89971081(S)-1-Bromo-5-fluoro-4-methyl-2-(pent-4-en-2-yloxy)benzeneYield 59%

Procedure

Prepared in 59% yield from 2-bromo-4-fluoro-5-methylphenol following the same procedure as (S)-1-bromo-4-fluoro-2-(pent-4-en-2-yloxy)benzene. 1H NMR (400 MHz, CDCl3) δ 7.21 (d, J=8.8 Hz, 1H), 6.75 (d, J=6.8 Hz, 1H), 5.91 (ddt, J=17.2, 10.2, 7.2 Hz, 1H), 5.20-5.07 (m, 2H), 4.42-4.26 (m, 1H), 2.60-2.48 (m, 1H), 2.45-2.37 (m, 1H), 2.23 (d, J=1.8 Hz, 3H), 1.33 (d, J=6.3 Hz, 3H).

Sources & evidence

ORD record
ord-3f54c87fae0f44c5b5abfa80a5c23f7a
Source dataset
uspto-grants-2016_08
Patent number
US09409922B2

Reaction notes

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