2,6-Difluorophenol → HCID 136088168, compound

HRID 2282784Notes

Reaction equation

HRID 2282784 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([C:11]([OH:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[N:14]([O-])=O.[Na+].[F:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[C:20]=1[OH:26]>O.Cl.[OH-].[K+]>[F:18][C:19]1[CH:24]=[C:23]([N:14]=[N:1][C:2]2[CH:10]=[C:9]([C:11]([OH:13])=[O:12])[CH:8]=[CH:7][C:3]=2[C:4]([OH:6])=[O:5])[CH:22]=[C:21]([F:25])[C:20]=1[OH:26]

Participants

7

Reactant 3

HCID 943922,6-DifluorophenolHCID 27248222-Aminoterephthalic acidHCID 23668193Sodium Nitrite

Product 1

HCID 136088168HCID 136088168, compoundYield 28.1%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolvent3×HCID 962WaterSolventHCID 14797Potassium HydroxideSolvent

Procedure

2-Aminoterephtalic acid (1.00 g, 5.52 mmol) was dissolved in hot mixture of 60 mL of water and 20 mL of conc. HCl. The solution was cooled in ice/NaCl bath to 0° C. giving a suspension of HCl salt. The solution of sodium nitrite (0.460 g, 6.67 mmol in 10 mL of water) was added dropwise to the suspension of ammonium salt, maintaining the temperature below +5° C. The resulting solution was stirred for 20 min and then added dropwise to the solution of 2,6-difluorophenol (0.720 g, 5.53 mmol) in 50 mL of 1M KOH, cooled in ice/water bath. The reaction mixture was stirred for 1.5 hrs in ice/water bath and then acidified with 10% HCl to pH 2-3. The resulting precipitate was collected, washed with water and dried in vacuum to give phenol 9 as an orange solid (0.5 g, 28%).

Workup

  1. customgiving
  2. temperaturemaintaining the temperature below +5° C
  3. customThe resulting precipitate was collected
  4. washwashed with water
  5. customdried in vacuum

Sources & evidence

ORD record
ord-d330cb53eb644ca8929362361abce600
Source dataset
uspto-grants-2015_09
Patent number
US09140706B2

Reaction notes

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