Hexamethylenetetramine → 3,5-Dibromosalicylaldehyde

HRID 1739468Notes

Reaction equation

HRID 1739468 reaction equation
C1N2CN3CN(C2)CN1C3.F[C:12](F)(F)[C:13]([OH:15])=O.[Br:18][C:19]1[CH:24]=[C:23]([Br:25])[CH:22]=C[C:20]=1[OH:26]>>[Br:18][C:19]1[C:20]([OH:26])=[C:12]([CH:22]=[C:23]([Br:25])[CH:24]=1)[CH:13]=[O:15]

Participants

4

Reactant 3

HCID 4101HexamethylenetetramineHCID 6422Trifluoroacetic acidHCID 120052,4-Dibromophenol

Product 1

HCID 70243,5-Dibromosalicylaldehyde

Conditions

Temperature
80 °C

Procedure

Hexamine (3.35 g, 23.92 mmol) was added portionwise to trifluoroacetic acid (25 ml) keeping the temperature below 40° C. with a water bath. 2,4-Dibromophenol was then added slowly and the reaction mixture heated at 80° C. for 31/2 hours. The reaction mixture was cooled, partially evaporated and then poured into ice/water. This mixture was stirred at ambient temperature overnight and the precipitate that formed filtered, dried and purified by chromatography (CH2Cl2 /hexane) to give the title compound (2.1 g).

Workup

  1. customthe temperature below 40° C.
  2. temperatureThe reaction mixture was cooled
  3. custompartially evaporated
  4. additionpoured into ice/water
  5. customthe precipitate that formed
  6. filtrationfiltered
  7. customdried
  8. custompurified by chromatography (CH2Cl2 /hexane)

Sources & evidence

ORD record
ord-b7ed080b4f7e485f9d9f4ce379477199
Source dataset
uspto-grants-1999_10
Patent number
US05965741

Reaction notes

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