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

HRID 535674Notes

Reaction equation

HRID 535674 reaction equation
[CH2:1]1N2CN3CN(C2)CN1C3.[Br:11][C:12]1[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=1[OH:19].[OH2:20].S(=O)(=O)(O)O>FC(F)(F)C(O)=O>[Br:11][C:12]1[C:13]([OH:19])=[C:14]([CH:15]=[C:16]([F:18])[CH:17]=1)[CH:1]=[O:20]

Participants

6

Reactant 4

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

Product 1

HCID 231489553-Bromo-5-fluoro-2-hydroxybenzaldehydeYield 83%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Hexamethylenetetramine (14.7 g, 105 mmol) was slowly added to a solution of 2-bromo-4-fluoro-phenol (10 g, 52.4 mmol) in trifluoroacetic acid (40 ml) at rt and heated to reflux for 18 h. The reaction mixture was cooled to rt and then water (60 ml) and sulfuric acid (30 ml, 50%) were added. The mixture was stirred for 3 h at rt and then extracted twice with ethyl acetate. The combined organic extracts were washed with 1N HCl, water, dried (Na2SO4), filtered and concentrated under reduced pressure to give 9.5 g (83%) of 3-bromo-5-fluoro-2-hydroxy-benzaldehyde.

Workup

  1. temperatureheated
  2. temperatureto reflux for 18 h
  3. extractionextracted twice with ethyl acetate
  4. washThe combined organic extracts were washed with 1N HCl, water
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e84803cfacd945858d3447e2321d3289
Source dataset
uspto-grants-2014_10
Patent number
US08859534B2

Reaction notes

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