Acetic Acid → 5-Bromo-2-fluorobenzaldehyde

HRID 2395606Notes

Reaction equation

HRID 2395606 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[C:4]([CH2:9]Br)[CH:3]=1.C(O)(=[O:13])C.C1N2CN3CN(C2)CN1C3.Cl>O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[C:4]([CH:3]=1)[CH:9]=[O:13]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 4101HexamethylenetetramineHCID 135532954-Bromo-2-(bromomethyl)-1-fluorobenzene

Product 1

HCID 7363275-Bromo-2-fluorobenzaldehyde

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 79.5 g (0.296 mol) of 4-bromo-2-bromomethyl-1-fluorobenzene (prepared according to G. E. Stokker, A. W. Alberts et al., J. Med. Chem., 1986, 29, 170), 126 ml of acetic acid, 82.7 g (0.59 mol) of hexamethylenetetramine and 126 ml of water is heated for 2 hours at reflux. The mixture is cooled to 90° C., 99.5 ml of concentrated hydrochloric acid are added and the mixture is heated for 30 min at reflux. Cooling, extraction with ether, washing with water, washing with an aqueous NaHCO3 solution, washing with water, drying over Na2SO4, filtration and evaporation under vacuum are carried out. The residue is purified by chromatography on silica (eluent: 10/1 hexane/ethyl acetate). Yd.: 23.6 g (39%)

Workup

  1. customprepared
  2. temperatureat reflux
  3. temperaturethe mixture is heated for 30 min
  4. temperatureat reflux
  5. temperatureCooling
  6. extractionextraction with ether
  7. washwashing with water
  8. washwashing with an aqueous NaHCO3 solution
  9. washwashing with water
  10. dry with materialdrying over Na2SO4, filtration and evaporation under vacuum
  11. customThe residue is purified by chromatography on silica (eluent: 10/1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-3b904829655b4633b2ff80a302901e62
Source dataset
uspto-grants-1996_02
Patent number
US05489592

Reaction notes

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