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

HRID 607201Notes

Reaction equation

HRID 607201 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 73B (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-2b17fd2395ef4279bf9f0b869232404e
Source dataset
uspto-grants-2011_03
Patent number
US07915411B2

Reaction notes

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