Boron tribromide → 4-Hydroxy-2,3-dimethylbenzaldehyde

HRID 62888Notes

Reaction equation

HRID 62888 reaction equation
C[O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[O:8])=[C:5]([CH3:11])[C:4]=1[CH3:12].B(Br)(Br)Br>C(Cl)Cl.O>[OH:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[O:8])=[C:5]([CH3:11])[C:4]=1[CH3:12]

Participants

5

Reactant 2

HCID 25134Boron tribromideHCID 5960582,3-Dimethyl-p-anisaldehyde

Product 1

HCID 146949984-Hydroxy-2,3-dimethylbenzaldehydeYield 10.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

4-Methoxy-2,3-dimethyl-benzaldehyde (2.0 g, 12.18 mmol) was dissolved in DCM (48 mL), and the solution was cooled to −78° C. 1M BBr3(24 mL, 24.13 mmol) was added slowly thereto, and the mixture was stirred at room temperature for 12 hours. After the termination of the reaction, the residue was diluted with water and extracted with DCM. The organic layer was dried with MgSO4 and concentrated under reduced pressure. The residue was purified by column chromatography (eluent, EtOAc/Hex=1/5) to obtain the title compound (187 mg, 10%).

Workup

  1. customAfter the termination of the reaction
  2. extractionextracted with DCM
  3. dry with materialThe organic layer was dried with MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography (eluent, EtOAc/Hex=1/5)

Sources & evidence

ORD record
ord-50f4ffecf7604cf3a11b2075c4e3aa30
Source dataset
uspto-grants-2016_09
Patent number
US09447044B2

Reaction notes

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