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

HRID 1664419Notes

Reaction equation

HRID 1664419 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-b996b5aa2f4647e1aa76ab82323a0b89
Source dataset
uspto-grants-2011_10
Patent number
US08039450B2

Reaction notes

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