Sodium Hydroxide → 4-Fluoro-2-methyl-5-nitrophenol

HRID 2065729Notes

Reaction equation

HRID 2065729 reaction equation
COC(=O)[O:4][C:5]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[C:8]([F:14])=[CH:7][C:6]=1[CH3:15].B(Br)(Br)Br.[OH-].[Na+]>ClCCl>[F:14][C:8]1[C:9]([N+:11]([O-:13])=[O:12])=[CH:10][C:5]([OH:4])=[C:6]([CH3:15])[CH:7]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 25134Boron tribromideHCID 144216192-Fluoro-5-methoxycarbonyloxy-4-methylnitrobenzene

Product 1

HCID 108210594-Fluoro-2-methyl-5-nitrophenolYield 81.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Carbonic acid 4-fluoro-2-methyl-5-nitro-phenyl ester methyl ester (1.8 g, 7.8 mmol) was dissolved in dichloromethane (100 ml) and cooled to 0° C. Boron tribromide (1 M in dichloromethane, 8 ml) was added. The mixture was allowed to warm to room temperature and was stirred overnight. To the solution was added 1N sodium hydroxide (25 ml) and the mixture was stirred vigorously for 1 hour. The layers were separated and the organic layer was dried over anhydrous sodium sulfate, and filtered and concentrated in vacuo to give 4-fluoro-2-methyl-5-nitro-phenol (1.083 g, 80.6%) as a red crystalline solid.

Workup

  1. temperatureto warm to room temperature
  2. stirringthe mixture was stirred vigorously for 1 hour
  3. customThe layers were separated
  4. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-12086ea04a2743fc8856b47578804ded
Source dataset
uspto-grants-2012_10
Patent number
US08288552B2

Reaction notes

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