Benzaldehyde → HCID 178516248, compound

HRID 2241319Notes

Reaction equation

HRID 2241319 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([F:9])[CH:3]=1.[CH:10](=O)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH:10](=[N:1]/[C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([F:9])[CH:3]=1)\[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 521998p-Toluenesulfonic acid monohydrateHCID 2735918Phenol, 4-amino-2-fluoro-

Product 1

HCID 178516248HCID 178516248, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred solution of 4-amino-2-fluorophenol (1.27 g, 10 mmol) in 30 mL of toluene at room temperature under nitrogen in a Dean Stark apparatus was added benzaldehyde (1.01 ml, 10 mmol) followed by p-toluenesulfonic acid monohydrate (38 mg, 0.2 mmol). The mixture was heated to reflux for 4 hours. The reaction was cooled to room temperature and a solid crystallized out of the reaction mixture. The mixture was cooled to 0° C. and then filtered and the solids rinsed with toluene. The isolated tan crystals were dried under high vacuum (1.5 gm, 70% yield).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 4 hours
  3. customa solid crystallized out of the reaction mixture
  4. temperatureThe mixture was cooled to 0° C.
  5. filtrationfiltered
  6. washthe solids rinsed with toluene
  7. customThe isolated tan crystals were dried under high vacuum (1.5 gm, 70% yield)

Sources & evidence

ORD record
ord-ad9871345ca04c19be09f1ff3b21eac3
Source dataset
uspto-grants-2010_05
Patent number
US07723330B2

Reaction notes

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