Benzyl Bromide → HCID 14857837, compound

HRID 1619168Notes

Reaction equation

HRID 1619168 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][CH:23]=1)[O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1/[C:13](=[CH:18]\[O:19][CH3:20])/[C:14]([O:16][CH3:17])=[O:15].[CH2:24](Br)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[CH2:24]([O:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][CH:23]=1)[O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1/[C:13](=[CH:18]\[O:19][CH3:20])/[C:14]([O:16][CH3:17])=[O:15])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 10925060HCID 10925060, compound

Product 1

HCID 14857837HCID 14857837, compoundYield 70.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of (E)-methyl 2-(2-((3-hydroxyphenoxy)methyl)phenyl)-3-methoxyacrylate (0.2 g, 0.63 mmol) obtained in Step 1, benzyl bromide (0.1 mL, 0.84 mmol) and cesium carbonate (0.31 g, 0.95 mmol) in 20 mL of acetonitrile (CH3CN) was stirred at room temperature for 3 hours after which the reaction solvent was removed by concentration in a vacuum. The residue was stirred in water (20 mL) and the aqueous layer was extracted twice with 20 mL of dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated in a vacuum. The concentrate was purified by silica gel chromatography to afford (E)-methyl 2-(2-((3-(benzyloxy)phenoxy)methyl)phenyl)-3-methoxyacrylate as a white solid (0.18 g, yield 70%).

Workup

  1. customwas removed by concentration in a vacuum
  2. extractionthe aqueous layer was extracted twice with 20 mL of dichloromethane
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in a vacuum
  6. customThe concentrate was purified by silica gel chromatography

Sources & evidence

ORD record
ord-8e5ff9e511bc465784e40711d4556c9a
Source dataset
uspto-grants-2014_07
Patent number
US08772290B2

Reaction notes

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