Sodium Nitrate → 5-BroMo-4-chloro-2-nitro-benzaldehyde

HRID 1955603Notes

Reaction equation

HRID 1955603 reaction equation
[N+:1]([O-:4])([O-])=[O:2].[Na+].[Br:6][C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][C:14]=1[Cl:15])[CH:10]=[O:11]>S(=O)(=O)(O)O>[Br:6][C:7]1[C:14]([Cl:15])=[CH:13][C:12]([N+:1]([O-:4])=[O:2])=[C:9]([CH:8]=1)[CH:10]=[O:11]

Participants

4

Reactant 2

HCID 24268Sodium NitrateHCID 140498093-Bromo-4-chlorobenzaldehyde

Product 1

HCID 153665485-BroMo-4-chloro-2-nitro-benzaldehydeYield 51.5%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a mixture of sulphuric acid (40 ml) and sodium nitrate (2.66 g, 31.3 mM) at 0°-5° C. was added 3-bromo-4-chlorobenzaldehyde (6.25 g, 28.5 mM). The resulting mixture was stirred at room temperature for 7 h and then diluted with ice water (300 ml). The precipitated solids were filtered, washed with water and dried to give a powder. Recrystallization of this material from the mixture of isopropanol and water (2:1) provided the title 2-nitrobenzaldehyde 1f (3.6 g, 51.5%) as a light yellow powder, m.p. 81°-82° C.

Workup

  1. filtrationThe precipitated solids were filtered
  2. washwashed with water
  3. customdried
  4. customto give a powder
  5. customRecrystallization of this material
  6. additionfrom the mixture of isopropanol and water (2:1)

Sources & evidence

ORD record
ord-3b6b2602f19f4f20a28d3bc63a1932d0
Source dataset
uspto-grants-1998_07
Patent number
US05776935

Reaction notes

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