Hydrogen Bromide → 4-Bromo-3-fluoro-2-hydroxybenzaldehyde

HRID 2272525Notes

Reaction equation

HRID 2272525 reaction equation
Br.[Br:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[O:8])=[C:5]([O:11]C)[C:4]=1[F:13]>C(O)(=O)C>[Br:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[O:8])=[C:5]([OH:11])[C:4]=1[F:13]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 840385064-Bromo-3-fluoro-2-methoxybenzaldehyde

Product 1

HCID 978894044-Bromo-3-fluoro-2-hydroxybenzaldehydeYield 70.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

48% Hydrobromic acid (254 mL) was added to a solution of 4-bromo-3-fluoro-2-methoxybenzaldehyde (52.3 g) in acetic acid (350 mL) at room temperature. The mixture was stirred at 120 C under nitrogen atmosphere for 16 hours and concentrated in vacuo. The residue was diluted with ethyl acetate and water. The mixture was extracted with ethyl acetate. The organic layer was separated, washed with water and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was triturated with diisopropyl ether and collected by filtration to give the title compound (34.6 g).

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe residue was diluted with ethyl acetate and water
  3. extractionThe mixture was extracted with ethyl acetate
  4. customThe organic layer was separated
  5. washwashed with water and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was triturated with diisopropyl ether
  9. filtrationcollected by filtration

Sources & evidence

ORD record
ord-5ddb39fda4284b778b095398304e21f4
Source dataset
uspto-grants-2015_09
Patent number
US09120777B2

Reaction notes

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