Hydrogen Bromide → 2-Bromo-4-fluoro-5-hydroxybenzaldehyde

HRID 1483729Notes

Reaction equation

HRID 1483729 reaction equation
[Br:1][C:2]1[CH:9]=[C:8]([F:10])[C:7]([O:11]C)=[CH:6][C:3]=1[CH:4]=[O:5].Br>C(O)(=O)C>[Br:1][C:2]1[CH:9]=[C:8]([F:10])[C:7]([OH:11])=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 231579072-Bromo-4-fluoro-5-methoxybenzaldehyde

Product 1

HCID 866364542-Bromo-4-fluoro-5-hydroxybenzaldehydeYield 64%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 2-bromo-4-fluoro-5-methoxybenzaldehyde (1.19 g, 8.20 mmol), 48% HBr (57 mL) and glacier acetic acid (57 mL) were refluxed at 130° C. for 5 hours. The glacier acetic acid was removed under reduced pressure. The solution was neutralized using sodium carbonate. Water was added and the mixture was extracted using ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and filtered. The solvent was removed under reduced pressure. The residue was purified by silica gel column using Combiflash to give 2-bromo-4-fluoro-5-hydroxybenzaldehyde (1.15 g, 64% yield).

Workup

  1. customThe glacier acetic acid was removed under reduced pressure
  2. additionWater was added
  3. extractionthe mixture was extracted
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customThe solvent was removed under reduced pressure
  8. customThe residue was purified by silica gel column

Sources & evidence

ORD record
ord-fd5986a1fe794a7b8ad6b08373c49477
Source dataset
uspto-grants-2016_08
Patent number
US09416146B2

Reaction notes

Loading…