Ethanol → 4-Bromo-3-fluorobenzaldehyde

HRID 346263Notes

Reaction equation

HRID 346263 reaction equation
C([O:4][CH:5](OC(=O)C)[C:6]1[CH:11]=[CH:10][C:9]([Br:12])=[C:8]([F:13])[CH:7]=1)(=O)C.C(O)C.O.S(=O)(=O)(O)O>CCOCC>[Br:12][C:9]1[CH:10]=[CH:11][C:6]([CH:5]=[O:4])=[CH:7][C:8]=1[F:13]

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 1118Sulfuric AcidHCID 536330654-Bromo-3-fluorobenzylidene diacetate

Product 1

HCID 27834114-Bromo-3-fluorobenzaldehyde

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 4-bromo-3-fluorobenzylidene diacetate (15 g), ethanol (41 ml), water (41 ml) and concentrated sulphuric acid (4 ml) was heated to reflux for 3 hours. After cooling, ether (300 ml) was added and the aqueous layer separated. The organic phase was washed with saturated sodium carbonate and brine before drying over anhydrous magnesium sulphate and evaporation in vacuo. 4-Bromo-3-fluorobenzaldehyde was obtained as a solid (7.3 g).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 3 hours
  3. temperatureAfter cooling
  4. customthe aqueous layer separated
  5. washThe organic phase was washed with saturated sodium carbonate and brine
  6. dry with materialbefore drying over anhydrous magnesium sulphate and evaporation in vacuo

Sources & evidence

ORD record
ord-b2bf3b052c1e4a8cba5a34f25d501af9
Source dataset
uspto-grants-1991_10
Patent number
US05061726

Reaction notes

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