N,N-Diethylaniline → 2-Allyl-3-bromo-6-chloro-5-(4-methoxybenzyl)phenol
Reaction equation
C([O:4][C:5]1[CH:10]=[C:9]([Br:11])[CH:8]=[C:7]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)[C:6]=1[Cl:21])C=C.CCN([C:27]1[CH:28]=CC=C[CH:32]=1)CC>>[CH2:28]([C:10]1[C:9]([Br:11])=[CH:8][C:7]([CH2:12][C:13]2[CH:14]=[CH:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=2)=[C:6]([Cl:21])[C:5]=1[OH:4])[CH:27]=[CH2:32]Participants
3
Procedure
A solution of 1-(allyloxy)-5-bromo-2-chloro-3-(4-methoxybenzyl)benzene (1.20 g, 3.26 mmol) in diethylaniline (3 mL) was heated in a sealed tube at 200° C. for 24 h under nitrogen atmosphere. The mixture was cooled to room temperature and quenched by slow addition of 1 M HCl (50-100 mL). The mixture was extracted with ethyl acetate (100-150 mL). The organic layer was dried over anhydrous MgSO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography to provide the compound 216 (1.10 g, 2.99 mmol, 92%).
Workup
- custom