2-Bromo-4-(trifluoromethoxy)phenol → (S)-2-Bromo-1-(pent-4-en-2-yloxy)-4-(trifluoromethoxy)benzene

HRID 1482086Notes

Reaction equation

HRID 1482086 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([O:8][C:9]([F:12])([F:11])[F:10])[CH:5]=[CH:4][C:3]=1[OH:13].Br[C:15]1[CH:20]=[C:19](F)C(F)=[CH:17][C:16]=1O[C@H](CC=C)C>>[Br:1][C:2]1[CH:7]=[C:6]([O:8][C:9]([F:11])([F:12])[F:10])[CH:5]=[CH:4][C:3]=1[O:13][C@H:20]([CH2:15][CH:16]=[CH2:17])[CH3:19]

Participants

3

Reactant 2

HCID 215840902-Bromo-4-(trifluoromethoxy)phenolHCID 118308806(S)-1-Bromo-4,5-difluoro-2-(pent-4-en-2-yloxy)benzene

Product 1

HCID 118308885(S)-2-Bromo-1-(pent-4-en-2-yloxy)-4-(trifluoromethoxy)benzeneYield 88%

Procedure

Prepared in 88% yield from 2-bromo-4-(trifluoromethoxy)phenol following the same procedure as (S)-1-bromo-4,5-difluoro-2-(pent-4-en-2-yloxy)benzene. 1H NMR (400 MHz, CDCl3) δ 7.45 (d, J=2.3 Hz, 1H), 7.13 (dd, J=8.9, 2.1 Hz, 1H), 6.90 (d, J=9.0 Hz, 1H), 5.90 (ddt, J=17.2, 10.1, 7.1 Hz, 1H), 5.22-5.09 (m, 2H), 4.50-4.35 (m, 1H), 2.63-2.48 (m, 1H), 2.48-2.36 (m, 1H), 1.37 (d, J=6.0 Hz, 3H).

Sources & evidence

ORD record
ord-132b7085941b4992b57730100aca667d
Source dataset
uspto-grants-2016_08
Patent number
US09409922B2

Reaction notes

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