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

HRID 576401Notes

Reaction equation

HRID 576401 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.C(N(CC)[C:25]1[CH:30]=CC=C[CH:26]=1)C>>[CH2:30]([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:25]=[CH2:26]

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 91%

Conditions

Temperature
200 °C

Procedure

The mixture of bromide 184 (2.52 g, 6.85 mmol) in N,N-diethylaniline (8 mL) was stirred at 200° C. for 45 hours. The mixture was cooled to rt and extracted with EtOAc/aq. 1N HCl solution (100 mL/100 mL). The organic layer was washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by silica gel column chromatography to provide the desired product 185 (2.3 g, 91%).

Workup

  1. temperatureThe mixture was cooled to rt
  2. extractionextracted with EtOAc/aq
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ce36f20688f54bcd84b71ddb0f5bde40
Source dataset
uspto-grants-2015_05
Patent number
US09034921B2

Reaction notes

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