3-Methoxy-2-nitrobenzaldehyde → 3-Hydroxy-2-nitrobenzaldehyde

HRID 858180Notes

Reaction equation

HRID 858180 reaction equation
C[O:2][C:3]1[C:4]([N+:11]([O-:13])=[O:12])=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH:6]=[O:7].B(Br)(Br)Br.C(Cl)Cl>C(Cl)Cl>[OH:2][C:3]1[C:4]([N+:11]([O-:13])=[O:12])=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH:6]=[O:7]

Participants

4

Reactant 2

HCID 988673-Methoxy-2-nitrobenzaldehydeHCID 22277759Boron tribromide dichloromethane

Product 1

HCID 137567473-Hydroxy-2-nitrobenzaldehydeYield 99.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

3.62 g of 3-methoxy-2-nitrobenzaldehyde was dissolved in 80 ml of methylene chloride and a boron tribromide-methylene chloride solution (15.03 g of boron tribromide, 40 ml of methylene chloride) was added dropwise under ice cooling, followed by stirring at 0° C. for one hour. The reaction solution was poured into ice, extracted with chloroform, dried and then concentrated to obtain 3.32 g of the desired compound.

Workup

  1. additionThe reaction solution was poured into ice
  2. extractionextracted with chloroform
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-776a122b75bd47f7afee9117bca6faaf
Source dataset
uspto-grants-2006_12
Patent number
US07148244B2

Reaction notes

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