Sodium Bicarbonate → 4-Bromo-2-fluoro-5-nitrophenol

HRID 639009Notes

Reaction equation

HRID 639009 reaction equation
C(=O)(OCC)[O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[C:6]([Br:12])=[CH:5][C:4]=1[F:13].C(=O)(O)[O-].[Na+]>CO>[Br:12][C:6]1[C:7]([N+:9]([O-:11])=[O:10])=[CH:8][C:3]([OH:2])=[C:4]([F:13])[CH:5]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 179763094-Bromo-2-fluoro-5-nitrophenyl ethyl carbonate

Product 1

HCID 179763164-Bromo-2-fluoro-5-nitrophenolYield 93.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4-bromo-2-fluoro-5-nitrophenyl ethyl carbonate (35 g, 113 mmole) in MeOH (200 mL) was treated with sodium bicarbonate (19 g, 227 mmole). The reaction mixture was stirred at 60 C for 4 hours. The methanol was evaporated under vacuum. Water (55 mL) was added to the residue and the aqueous layer was acidified to pH=5 by addition of a solution of 6N hydrogen chloride. The aqueous layer was extracted twice with ethyl acetate. The combined organic layers were dried over magnesium sulfate and evaporated under vacuum to afford the title compound (25 g, 93%) as a yellow solid. LC-MS (ES) (M+H)+ m/z=237.

Workup

  1. customThe methanol was evaporated under vacuum
  2. additionWater (55 mL) was added to the residue
  3. additionthe aqueous layer was acidified to pH=5 by addition of a solution of 6N hydrogen chloride
  4. extractionThe aqueous layer was extracted twice with ethyl acetate
  5. dry with materialThe combined organic layers were dried over magnesium sulfate
  6. customevaporated under vacuum

Sources & evidence

ORD record
ord-9e5c7b314094459da1a09e727fd7d1ad
Source dataset
uspto-grants-2010_04
Patent number
US07691850B2

Reaction notes

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