Phenol → HCID 22614274, compound

HRID 842552Notes

Reaction equation

HRID 842552 reaction equation
Br[CH2:2][C:3]1[C:4]([Cl:17])=[C:5]([CH:10]=[CH:11][C:12]=1[S:13]([CH3:16])(=[O:15])=[O:14])[C:6]([O:8]C)=[O:7].[C:18]1([OH:24])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[H-].[Na+].[OH-].[Na+]>CN(C)C=O.O>[Cl:17][C:4]1[C:3]([CH2:2][O:24][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:12]([S:13]([CH3:16])(=[O:15])=[O:14])[CH:11]=[CH:10][C:5]=1[C:6]([OH:8])=[O:7]

Participants

7

Reactant 4

HCID 996PhenolHCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 10969914Methyl 3-bromomethyl-2-chloro-4-methylsulfonylbenzoate

Product 1

HCID 22614274HCID 22614274, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

1.0 g (2.93 mmol) of methyl 3-bromomethyl-2-chloro-4-methylsulfonylbenzoate and 0.28 g (2.93 mmol) of phenol were dissolved in 20 ml of dimethylformamide and treated with 0.14 g (3.51 mmol) of 60% strength sodium hydride. The mixture was stirred overnight at room temperature and then concentrated in a high vacuum on a rotary evaporator. The residue was dissolved in 16 ml of tetrahydrofuran and 8 ml of water and the solution was refluxed for 4 h together with 0.23 g of NaOH (5.85 mmol). It was then allowed to cool and was largely concentrated on a rotary evaporator, and the aqueous residue was then treated with 2 M HCl. It was then extracted with methylene chloride, and the combined organic phase was dried over MgSO4 and completely concentrated on a rotary evaporator.

Workup

  1. concentrationconcentrated in a high vacuum on a rotary evaporator
  2. dissolutionThe residue was dissolved in 16 ml of tetrahydrofuran
  3. temperatureto cool
  4. concentrationwas largely concentrated on a rotary evaporator
  5. additionthe aqueous residue was then treated with 2 M HCl
  6. extractionIt was then extracted with methylene chloride
  7. dry with materialthe combined organic phase was dried over MgSO4
  8. concentrationcompletely concentrated on a rotary evaporator

Sources & evidence

ORD record
ord-2db6412ce11b480fadddc0454b26269c
Source dataset
uspto-grants-2002_04
Patent number
US06376429B1

Reaction notes

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