Allyl bromide → 1-Bromo-2-allyloxy-4-fluorobenzene

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[OH:9].C(=O)([O-])[O-].[K+].[K+].[CH2:16](Br)[CH:17]=[CH2:18]>>[CH2:18]([O:9][C:3]1[CH:4]=[C:5]([F:8])[CH:6]=[CH:7][C:2]=1[Br:1])[CH:17]=[CH2:16]

Participants

Reactant 3

HCID 7841Allyl bromide

HCID 11430Potassium Carbonate

HCID 27246002-Bromo-5-fluorophenol

Product 1

HCID 666546401-Bromo-2-allyloxy-4-fluorobenzeneYield 100.7%

Procedure

Treatment of 2-bromo-5-fluorophenol (10.00 g, 0.052 mol) with potassium carbonate (29.30 g, 0.209 mol) and allyl bromide (7.60 g, 0.063 mol) generally according to the reaction procedure described for Intermediate 8 provided 12.1 g (99%) of 2-(allyloxy)-1-bromo-4-fluorobenzene as a colorless oil. Rf=0.37 (silica, ethyl acetate:hexanes 1:9); 1H NMR (DMSO-d6) δH 7.58 (dd, 1H); 7.05 (dd, 1H); 6.75 (dt, 1H); 6.02 (m, 1H); 5.43 (d, 1H); 5.27 (d, 1H); 4.65 (m, 2H).

Sources & evidence

ORD record: ord-4bbab62409b1496898278c8c549a7982
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07435837B2

Reaction notes

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