N,N-Diethylaniline → 2-Allyl-3-bromo-6-chloro-5-(4-methoxybenzyl)phenol

HRID 2206783Notes

Reaction equation

HRID 2206783 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

Reactant 2

HCID 7061N,N-DiethylanilineHCID 867140811-(Allyloxy)-5-bromo-2-chloro-3-(4-methoxybenzyl)benzene

Product 1

HCID 867140802-Allyl-3-bromo-6-chloro-5-(4-methoxybenzyl)phenolYield 92%

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

  1. customquenched by slow addition of 1 M HCl (50-100 mL)
  2. extractionThe mixture was extracted with ethyl acetate (100-150 mL)
  3. dry with materialThe organic layer was dried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ec77ce2093384d34bc0f642e795a2437
Source dataset
uspto-grants-2016_06
Patent number
US09371303B2

Reaction notes

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