Boron tribromide → Benzaldehyde, 2,3-dihydroxy-4-nitro-

HRID 2055017Notes

Reaction equation

HRID 2055017 reaction equation
[OH:1][C:2]1[C:9]([O:10]C)=[C:8]([N+:12]([O-:14])=[O:13])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].B(Br)(Br)Br>ClCCl>[OH:1][C:2]1[C:9]([OH:10])=[C:8]([N+:12]([O-:14])=[O:13])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 1497744720041-61-6

Product 1

HCID 10442360Benzaldehyde, 2,3-dihydroxy-4-nitro-Yield 95.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

17.2 g of 2-hydroxy-3-methoxy-4-nitrobenzaldehyde (J. Het. Chem. 33, (1996), 1171) in 350 ml of dichloromethane is slowly mixed at 0° C. with 175 ml of boron tribromide solution (1 M in dichloromethane), and it is stirred for another 4 hours. The batch is added to ice water, the organic phase is separated, and the aqueous phase is extracted with dichloromethane. The combined organic phases are washed with water, and the solvent is removed in a vacuum. 15.2 g of 2,3-dihydroxy-4-nitrobenzaldehyde is obtained as a red solid, flash point 122-126° C.

Workup

  1. customthe organic phase is separated
  2. extractionthe aqueous phase is extracted with dichloromethane
  3. washThe combined organic phases are washed with water
  4. customthe solvent is removed in a vacuum

Sources & evidence

ORD record
ord-531a81c9364047809724090e922097bd
Source dataset
uspto-grants-2008_02
Patent number
US07329753B2

Reaction notes

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