Water → 3-Bromo-5-fluoro-2-hydroxybenzaldehyde

HRID 335571Notes

Reaction equation

HRID 335571 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[OH:9].[CH2:10]1N2CN3CN(C2)CN1C3.[OH2:20].S(=O)(=O)(O)O>C(O)(C(F)(F)F)=O>[Br:1][C:2]1[C:3]([OH:9])=[C:4]([CH:5]=[C:6]([F:8])[CH:7]=1)[CH:10]=[O:20]

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 4101HexamethylenetetramineHCID 6054722-Bromo-4-fluorophenol

Product 1

HCID 231489553-Bromo-5-fluoro-2-hydroxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

1.0 g (5.24 mmol) of 2-bromo-4-fluorophenol is initially charged in 4 ml of TFA. Over a period of 20 min, 1.47 g (10.47 mmol) of hexamethylenetetramine are added a little at a time. The mixture is then heated under reflux for 28 h. At RT, 6 ml of water and 3 ml of 50% strength sulfuric acid are added. After 2 h at RT, the reaction mixture is extracted twice with in each case 30 ml of ethyl acetate. The combined organic phases are washed four times with 1N hydrochloric acid and once with water and then dried over magnesium sulfate. The crude product is reacted further without further purification.

Workup

  1. temperatureThe mixture is then heated
  2. temperatureunder reflux for 28 h
  3. waitAfter 2 h at RT
  4. extractionthe reaction mixture is extracted twice with in each case 30 ml of ethyl acetate
  5. washThe combined organic phases are washed four times with 1N hydrochloric acid
  6. dry with materialonce with water and then dried over magnesium sulfate
  7. customThe crude product is reacted further without further purification

Sources & evidence

ORD record
ord-691c82a93be84c83b19c0a32832991e3
Source dataset
uspto-grants-2014_11
Patent number
US08884017B2

Reaction notes

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