p-Xylyl bromide → HCID 86673392, compound

HRID 1023359Notes

Reaction equation

HRID 1023359 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12](/[CH:15]=[CH:16]/[C:17]([O:19][CH2:20][CH2:21][CH2:22][CH3:23])=[O:18])=[C:11]([CH3:24])[CH:10]=2)=[N:6][CH:7]=1.[H-].[Na+].Br[CH2:28][C:29]1[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][CH:30]=1.[NH4+].[Cl-]>CN(C=O)C>[CH3:24][C:11]1[CH:10]=[C:9]([O:8][C:5]2[CH:4]=[CH:3][C:2]([O:1][CH2:28][C:29]3[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][CH:30]=3)=[CH:7][N:6]=2)[CH:14]=[CH:13][C:12]=1/[CH:15]=[CH:16]/[C:17]([O:19][CH2:20][CH2:21][CH2:22][CH3:23])=[O:18]

Participants

6

Reactant 4

HCID 7721p-Xylyl bromideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 67327622HCID 67327622, compound

Product 1

HCID 86673392HCID 86673392, compoundYield 101.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a DMF (40 mL) solution of butyl (E)-3-{4-[(5-hydroxypyridin-2-yl)oxy]-2-methylphenyl}prop-2-enoate (3.54 g) was added NaH (60% in oil) (467 mg) at 0 ° C. After stirring for 10 minutes, 1-(bromomethyl)-4-methylbenzene (2.10 g) was added, and the resultant mixture was stirred at room temperature for 3.5 hours. To the reaction mixture was added saturated aqueous NH4Cl, and extracted with AcOEt. The organic layer was washed with water, saturated aqueous NaCl, dried over anhydrous Na2SO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane/AcOEt =9/1 to 3/1) to afford butyl (E)-3-[2-methyl-4-({5-[(4-methylbenzyl)oxy]pyridin-2-yl}oxy)phenyl]prop-2-enoate as a yellow solid (4.72 g).

Workup

  1. extractionextracted with AcOEt
  2. washThe organic layer was washed with water, saturated aqueous NaCl
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (n-hexane/AcOEt =9/1 to 3/1)

Sources & evidence

ORD record
ord-d50af1bd616d4dc7ae857a3387e8fbc1
Source dataset
uspto-grants-2014_05
Patent number
US08722663B2

Reaction notes

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