Methyl 2-bromo-4-fluoro-5-nitrophenoxyformate → 2-Bromo-4-fluoro-5-nitrophenol

HRID 619886Notes

Reaction equation

HRID 619886 reaction equation
C(=O)(OC)[O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[C:6]([F:12])=[CH:5][C:4]=1[Br:13]>[OH-].[Na+]>[Br:13][C:4]1[CH:5]=[C:6]([F:12])[C:7]([N+:9]([O-:11])=[O:10])=[CH:8][C:3]=1[OH:2]

Participants

3

Reactant 1

HCID 13268178Methyl 2-bromo-4-fluoro-5-nitrophenoxyformate

Product 1

HCID 132681792-Bromo-4-fluoro-5-nitrophenolYield 65.7%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A stirred solution of 1031 g (3.5 moles) of 2-bromo-4-fluoro-5-nitrophenyl methyl carbonate in 300 mL of 2.3N aqueous sodium hydroxide was heated to reflux and stirred for three hours. The hot reaction mixture was filtered through diatomaceous earth. Any material remaining in the reaction vessel was washed onto the filter cake with 1000 mL of water. The filtrate was cooled to 8°-10° C., and 560 mL of concentrated hydrochloric acid was added, with stirring, over one hour. The resultant solid was collected by filtration. Any material remaining in the reaction vessel was washed onto the filter cake with 1000 mL of water. The dried filter cake was recrystallized from toluene to give, in two crops, 543 g of 2-bromo-4-fluoro-5-nitrophenol, m.p. 124°-126° C.

Workup

  1. temperatureto reflux
  2. filtrationThe hot reaction mixture was filtered through diatomaceous earth
  3. washwas washed onto the filter cake with 1000 mL of water
  4. temperatureThe filtrate was cooled to 8°-10° C.
  5. addition560 mL of concentrated hydrochloric acid was added
  6. stirringwith stirring, over one hour
  7. filtrationThe resultant solid was collected by filtration
  8. washwas washed onto the filter cake with 1000 mL of water
  9. filtrationThe dried filter cake
  10. customwas recrystallized from toluene

Sources & evidence

ORD record
ord-e432e386a9754b1e8be117ac24f4f915
Source dataset
uspto-grants-1989_04
Patent number
US04818276

Reaction notes

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