3-Bromo-4-fluorobenzyl Alcohol → 3-Bromo-4-fluorobenzaldehyde

HRID 231316Notes

Reaction equation

HRID 231316 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[F:10])[CH2:5][OH:6]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[F:10])[CH:5]=[O:6]

Participants

3

Reactant 1

HCID 27733513-Bromo-4-fluorobenzyl Alcohol

Product 1

HCID 1736043-Bromo-4-fluorobenzaldehydeYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 45.9 g (0.225 mol) of 3-bromo-4-fluoro-benzyl alcohol in 45 ml of methylene chloride was added dropwise to a suspension of 78 g of pyridine/CrO3 /HCl in 450 ml of methylene chloride. During this addition, the temperature of the mixture rose to about 40° C. The mixture was then subsequently stirred for 1 hour, the organic phase was decanted from the chromium salts and the solvent was distilled off in vacuo. The residue was distilled. 39 g (86% of theory) of 3-bromo-4-fluoro-benzaldehyde with a boiling point of 63°-65° C./0.3 mm Hg were thus obtained.

Workup

  1. additionDuring this addition
  2. customrose to about 40° C
  3. customthe organic phase was decanted from the chromium salts
  4. distillationthe solvent was distilled off in vacuo
  5. distillationThe residue was distilled

Sources & evidence

ORD record
ord-7f0fffc1c03b463f95a93d836f483e99
Source dataset
uspto-grants-1989_07
Patent number
US04845249

Reaction notes

Loading…