Allyl bromide → 1-(2-(Allyloxy)ethoxy)-2-bromo-5-chloro-4-(4-ethylbenzyl)benzene

HRID 1175319Notes

Reaction equation

HRID 1175319 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][CH3:20])=[CH:15][CH:14]=2)[C:9]([Cl:21])=[CH:8][C:3]=1[O:4][CH2:5][CH2:6][OH:7].[H-].[Na+].[CH2:24](Br)[CH:25]=[CH2:26]>CN(C=O)C>[CH2:26]([O:7][CH2:6][CH2:5][O:4][C:3]1[CH:8]=[C:9]([Cl:21])[C:10]([CH2:12][C:13]2[CH:14]=[CH:15][C:16]([CH2:19][CH3:20])=[CH:17][CH:18]=2)=[CH:11][C:2]=1[Br:1])[CH:25]=[CH2:24]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 595577142-(2-Bromo-5-chloro-4-(4-ethylbenzyl)phenoxy)ethanol

Product 1

HCID 595577091-(2-(Allyloxy)ethoxy)-2-bromo-5-chloro-4-(4-ethylbenzyl)benzeneYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(2-bromo-5-chloro-4-(4-ethylbenzyl)phenoxy)ethanol (AU) (1.85 g, 5 mmol) in anhydrous DMF (10 mL), NaH (0.36 g 15 mmol) was added in portions, and the mixture was stirred at room temperature for 2 hours. Then allyl bromide (1.82 g, 15 mmol) was added dropwise, and the mixture was heated to 45° C. overnight. The reaction was quenched with the saturated NH4Cl and the mixture was extracted with EtOAc, and then washed with water and brine. After drying with anhydrous Na2SO4, the organic portion was filtered and concentrated. The residue was purified by flash chromatography to give AV as an oil (1.74 g, yield 85%). 1H-NMR (CDCl3, 300 MHz) δ 7.31 (s, 1H), 7.13 (m, 4H), 6.94 (s, 1H), 5.94 (m, 1H), 5.26 (m, 2H), 4.14 (m, 4H), 3.96 (s, 2H), 3.84 (m, 2H), 2.64 (q, J=7.5 Hz, 2H), 1.22 (t, J=7.5 Hz, 3H).

Workup

  1. temperaturethe mixture was heated to 45° C. overnight
  2. customThe reaction was quenched with the saturated NH4Cl
  3. extractionthe mixture was extracted with EtOAc
  4. washwashed with water and brine
  5. dry with materialAfter drying with anhydrous Na2SO4
  6. filtrationthe organic portion was filtered
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-be2cfe62a028479a99bf001549c84027
Source dataset
uspto-grants-2010_11
Patent number
US07838498B2

Reaction notes

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