Ammonia → 4-Fluoro-2-methyl-5-nitrophenol

HRID 393590Notes

Reaction equation

HRID 393590 reaction equation
N.C(=O)(OC)[O:3][C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[C:7]([F:13])=[CH:6][C:5]=1[CH3:14]>CO>[F:13][C:7]1[C:8]([N+:10]([O-:12])=[O:11])=[CH:9][C:4]([OH:3])=[C:5]([CH3:14])[CH:6]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 144216192-Fluoro-5-methoxycarbonyloxy-4-methylnitrobenzene

Product 1

HCID 108210594-Fluoro-2-methyl-5-nitrophenolYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Concentrated aqueous ammonia solution (30 ml) was added to a solution of (4-fluoro-2-methyl-5-nitrophenyl) methyl carbonate (6 g, 26 mmol), (prepared as described in EP 0307777 A2), in methanol (150 ml) and the mixture stirred for 1 hour at ambient temperature. Most of the organic solvent was removed by evaporation and the residue was partitioned between water and ethyl acetate. The organic layer was separated, dried (MgSO4) and the volatiles removed by evaporation to give 4-fluoro-2-methyl-5-nitrophenol (4.45 g, 100%).

Workup

  1. customMost of the organic solvent was removed by evaporation
  2. customthe residue was partitioned between water and ethyl acetate
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. customthe volatiles removed by evaporation

Sources & evidence

ORD record
ord-26e2b64f56cc4d79896ecb5e76486d8f
Source dataset
uspto-grants-2004_10
Patent number
US06809097B1

Reaction notes

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