Sodium Bicarbonate → Phenol, 2-chloro-4-fluoro-5-nitro-

HRID 883927Notes

Reaction equation

HRID 883927 reaction equation
C(OC(=O)[O:5][C:6]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[C:9]([F:15])=[CH:8][C:7]=1[Cl:16])C.C(=O)(O)[O-].[Na+]>CO.O>[Cl:16][C:7]1[CH:8]=[C:9]([F:15])[C:10]([N+:12]([O-:14])=[O:13])=[CH:11][C:6]=1[OH:5]

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 37297642-chloro-4-fluoro-5-nitrophenyl ethyl carbonate

Product 1

HCID 158655Phenol, 2-chloro-4-fluoro-5-nitro-Yield 98.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of the product from Example 47B (0.87 g, 3.30 mmol) in methanol (20 mL) and water (1 mL) was added sodium bicarbonate (2.22 g, 26.4 mmol) and the mixture stirred at room temperature for 16 hours. The methanol was then removed under vacuum, dichloromethane (20 mL) was added to the mixture, the organic solution was washed with brine (50 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated under vacuum to provide the title product (0.62 g, 98%).

Workup

  1. customThe methanol was then removed under vacuum, dichloromethane (20 mL)
  2. additionwas added to the mixture
  3. washthe organic solution was washed with brine (50 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-456294c6a5014e529f165d3b7545cb69
Source dataset
uspto-grants-2012_08
Patent number
US08236950B2

Reaction notes

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