Citric Acid → 4-Fluoro-5-iodo-2-methoxyphenol

HRID 1438134Notes

Reaction equation

HRID 1438134 reaction equation
C([O:4][C:5]1[CH:10]=[C:9]([I:11])[C:8]([F:12])=[CH:7][C:6]=1[O:13][CH3:14])(=O)C.[OH-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1.CO>[F:12][C:8]1[C:9]([I:11])=[CH:10][C:5]([OH:4])=[C:6]([O:13][CH3:14])[CH:7]=1

Participants

6

Reactant 3

HCID 311Citric AcidHCID 14798Sodium HydroxideHCID 59838025HCID 59838025, compound

Product 1

HCID 598380024-Fluoro-5-iodo-2-methoxyphenolYield 100%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 64B (680 mg, 2.19 mmol) in THF (3.0 mL) and MeOH (1.0 mL) was added 1.0 N NaOH (2.74 mL, 2.74 mmol). The reaction was stirred at rt for 2.0 h before it was acidified by addition of 5% citric acid. The mixture was extracted with EtOAc, washed with brine and dried over Na2SO4. After evaporation of the solvent, 64C (586 mg, 100% yield) was obtained as a solid and used for next step without further purification. 1H NMR (400 MHz, CDCl3) δ ppm 3.85 (s, 3H) 6.62 (d, J=8.79 Hz, 1H) 7.21 (d, J=6.15 Hz, 1H).

Workup

  1. extractionThe mixture was extracted with EtOAc
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. customAfter evaporation of the solvent

Sources & evidence

ORD record
ord-79e9f5ccd88e4338a7588162735ddf5c
Source dataset
uspto-grants-2009_11
Patent number
US07622585B2

Reaction notes

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