2-Bromo-4,5-dimethylphenol → (S)-1-Bromo-4,5-dimethyl-2-(pent-4-en-2-yloxy)benzene

HRID 1482027Notes

Reaction equation

HRID 1482027 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[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]([CH3:8])[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 1409612-Bromo-4,5-dimethylphenolHCID 118308842(S)-1-Bromo-4-fluoro-2-(pent-4-en-2-yloxy)benzene

Product 1

HCID 89971250(S)-1-Bromo-4,5-dimethyl-2-(pent-4-en-2-yloxy)benzeneYield 59%

Procedure

Prepared in 59% yield from 2-bromo-4,5-dimethylphenol following the same procedure as (S)-1-bromo-4-fluoro-2-(pent-4-en-2-yloxy)benzene. 1H NMR (400 MHz, CDCl3) δ 7.30 (s, 1H), 6.73 (s, 1H), 5.92 (ddt, J=17.2, 10.1, 7.1 Hz, 1H), 5.19-5.09 (m, 2H), 4.44-4.33 (m, 1H), 2.59-2.49 (m, 1H), 2.45-2.37 (m, 1H), 2.21 (s, 3H), 2.18 (s, 3H), 1.34 (d, J=6.0 Hz, 3H).

Sources & evidence

ORD record
ord-9ea72ee9b7d141afb7c6812d8dc572ce
Source dataset
uspto-grants-2016_08
Patent number
US09409922B2

Reaction notes

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