Hexamethylenetetramine → 3,5-Difluoro-4-hydroxybenzaldehyde

HRID 62833

Reaction equation

HRID 62833 reaction equation
[C:1](O)(C(F)(F)F)=[O:2].[F:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([F:15])[C:10]=1[OH:16].C1N2CN3CN(C2)CN1C3>O>[F:8][C:9]1[CH:14]=[C:13]([CH:12]=[C:11]([F:15])[C:10]=1[OH:16])[CH:1]=[O:2]

Participants

5

Reactant 3

HCID 4101HexamethylenetetramineHCID 6422Trifluoroacetic acidHCID 943922,6-Difluorophenol

Product 1

HCID 101925843,5-Difluoro-4-hydroxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

TFA (7 mL) was added to 2,6-difluoro-phenol (1.0 g, 7.69 mmol) and hexam-ethylenetetraamine (1.08 g, 7.69 mmol), and the mixture was stirred at 75˜80° C. for 12 hours. The reactant was cooled, diluted with water, and then extracted with DCM/MeOH (9:1) solution three or four times. The organic layer was concentrated under reduced pressure, and DCM was added to the residue. The mixture was dried with MgSO4 and concentrated under reduced pressure. The reaction product was used in the next step without a separate purification process.

Workup

  1. temperatureThe reactant was cooled
  2. extractionextracted with DCM/MeOH (9:1) solution three or four times
  3. concentrationThe organic layer was concentrated under reduced pressure, and DCM
  4. additionwas added to the residue
  5. dry with materialThe mixture was dried with MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customThe reaction product was used in the next step without a separate purification process

Sources & evidence

ORD record
ord-027e21b1ee4d42b3bf74111e4af661b8
Source dataset
uspto-grants-2016_09
Patent number
US09447044B2

Linked notes

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