Boron tribromide → 2-Fluoro-4,6-dihydroxybenzaldehyde

HRID 217460Notes

Reaction equation

HRID 217460 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([O:10]C)[CH:7]=[C:6]([O:12]C)[C:3]=1[CH:4]=[O:5].B(Br)(Br)Br>C(Cl)Cl>[F:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[C:6]([OH:12])[C:3]=1[CH:4]=[O:5]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 153851372-Fluoro-4,6-dimethoxybenzaldehyde

Product 1

HCID 220104032-Fluoro-4,6-dihydroxybenzaldehydeYield 64.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2-Fluoro-4,6-dimethoxybenzaldehyde (22 g) was dissolved in DCM (110 mL), and a solution of BBr3 in DCM (1 M, 300 mL) was added dropwise thereto under ice-cooling, followed by stirring at room temperature overnight. After confirming completion of the reaction, the reaction liquid was poured into ice-water (100 mL), followed by stirring for 1 hour and then extracting with EtOAc three times. The organic layer was combined, washed with water and brine in this order, dried over MgSO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (automatic purification device, hexane:EtOAc=80:20 to 60:40) to obtain 2-fluoro-4,6-dihydroxybenzaldehyde (12 g) as a white powder.

Workup

  1. temperatureunder ice-cooling
  2. customcompletion of the reaction
  3. customthe reaction liquid
  4. stirringby stirring for 1 hour
  5. extractionextracting with EtOAc three times
  6. washwashed with water and brine in this order
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (automatic purification device, hexane:EtOAc=80:20 to 60:40)

Sources & evidence

ORD record
ord-abad849adfd74541942976d50590e923
Source dataset
uspto-grants-2012_06
Patent number
US08193378B2

Reaction notes

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