Formic Acid → 2-Chloro-4-fluorobenzaldehyde

HRID 231422Notes

Reaction equation

HRID 231422 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:3]=1[CH:4](Br)Br.C(O)=[O:13].Cl>>[Cl:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:3]=1[CH:4]=[O:13]

Participants

4

Procedure

In a flask were placed 30.25 g (0.100 mole) of 2-chloro-4-fluorobenzal bromide, 45 ml (1.2 mole) of formic acid, and 15 ml of concentrated hydrochloric acid. This mixture was heated at 100°-105° C. overnight. After cooling to room temperature, the reaction mixture was poured into 200 ml of an ice/water mixture which was then extracted twice with diethyl ether. The combined extracts were washed successively with a saturated, aqueous, sodium bicarbonate solution and water. After being dried over anhydrous magnesium sulfate, the extract was filtered, and the solvent was evaporated under reduced pressure, leaving 17 g of 2-chloro-4-fluorobenzaldehyde as a residue.

Workup

  1. customIn a flask were placed
  2. temperatureThis mixture was heated at 100°-105° C. overnight
  3. extractionwas then extracted twice with diethyl ether
  4. washThe combined extracts were washed successively with a saturated, aqueous, sodium bicarbonate solution and water
  5. dry with materialAfter being dried over anhydrous magnesium sulfate
  6. filtrationthe extract was filtered
  7. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-c96fdab71ea54d868976dcd54163cebf
Source dataset
uspto-grants-1989_07
Patent number
US04846882

Reaction notes

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