Sodium hydride → HCID 23017946, compound

HRID 1788366Notes

Reaction equation

HRID 1788366 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([O:9][CH3:10])[CH:5]=[C:6]([CH3:8])[CH:7]=1.BrN1C(=O)CCC1=O.[CH3:19][S:20]([C:23]1[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=1)(=[O:22])=[O:21].[H-].[Na+]>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.CCCCCC.O>[CH3:19][S:20]([C:23]1[CH:28]=[CH:27][C:26]([O:29][CH2:1][C:2]2[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([O:9][CH3:10])[CH:3]=2)=[CH:25][CH:24]=1)(=[O:21])=[O:22]

Participants

9

Reactant 4

HCID 24758Sodium hydrideHCID 67184N-bromobutanimideHCID 701263,5-DimethylanisoleHCID 1233504-(Methylsulfonyl)phenol

Product 1

HCID 23017946HCID 23017946, compoundYield 56.3%

Reagents, catalysts & solvents 4

HCID 7187Benzoyl PeroxideCatalystHCID 962WaterSolventHCID 5943Carbon TetrachlorideSolventHCID 8058HexaneSolvent

Procedure

To a solution of 5.0 g (36.7 mmol) of 3,5-dimethylanisole in carbon tetrachloride (35 mL) was added 5.2 g (29.4 mmol) of N-bromosuccinimide and 0.2 g (0.74 mmol) of benzoyl peroxide at room temperature, followed by heating under reflux for 2 hours. The reaction mixture was left standing to cool and then filtered. The filtrate was concentrated under a reduced pressure. The obtained residue was dissolved in ethanol (7.5 mL), and treated with 4.5 g (26.1 mmol) of 4-methylsulfonylphenol and 7.5 mL (30.0 mmol) of a 4 N aqueous sodium hydride, and heated under reflux for 1 hour. After standing to cool, water and hexane was added to the reaction mixture, and the precipitates were collected by filtration and washed with ether. The residue was purified by column chromatography (silica gel 80 g, developing solvent: chloroform-ethyl acetate=4: 1) to obtain 4.5 g (yield 40.4%) of 1-(4-methanesulfonylphenoxymethy)-3-methoxy-5-methylbenzene (VI-7) as a colorless crystal. Its physical properties are shown below.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 2 hours
  3. waitThe reaction mixture was left
  4. temperatureto cool
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under a reduced pressure
  7. dissolutionThe obtained residue was dissolved in ethanol (7.5 mL)
  8. temperatureheated
  9. temperatureunder reflux for 1 hour
  10. temperatureto cool
  11. filtrationthe precipitates were collected by filtration
  12. washwashed with ether
  13. customThe residue was purified by column chromatography (silica gel 80 g, developing solvent: chloroform-ethyl acetate=4: 1)

Sources & evidence

ORD record
ord-56ab754a640d492095216eb4c3a41332
Source dataset
uspto-grants-2009_03
Patent number
US07511144B2

Reaction notes

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