Hydrogen Bromide → Benzaldehyde, 2,3-dihydroxy-4-nitro-

HRID 218271Notes

Reaction equation

HRID 218271 reaction equation
C([O:4][C:5]1[C:12]([O:13]C)=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=[CH:9][C:6]=1[CH:7]=[O:8])(=O)C.Br>C(O)(=O)C>[OH:4][C:5]1[C:12]([OH:13])=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=[CH:9][C:6]=1[CH:7]=[O:8]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 21783433HCID 21783433, compound

Product 1

HCID 10442360Benzaldehyde, 2,3-dihydroxy-4-nitro-Yield 91%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
150 °C

Procedure

43 (2.5 g, 10.5 mmol) was added to a solution of acetic acid (62.5 mL) and hydrobromic acid 48% (70 mL) and the reaction mixture was heated at 150° C. for 4 h. The reaction mixture was then cooled to rt and evaporated to dryness. The residue was diluted in hot CH2Cl2 (40 mL) and filtered. The filtrate was evaporated to dryness to give 44 (1.74 g, 91%) which was used as such in the next step:

Workup

  1. temperatureThe reaction mixture was then cooled to rt
  2. customevaporated to dryness
  3. additionThe residue was diluted in hot CH2Cl2 (40 mL)
  4. filtrationfiltered
  5. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-ff0c615cad7d4dd096e5f930998f45a0
Source dataset
uspto-grants-2012_06
Patent number
US08198302B2

Reaction notes

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