Sodium Nitrate → 4-Bromo-3-nitrobenzaldehyde

HRID 1837088Notes

Reaction equation

HRID 1837088 reaction equation
[N+:1]([O-:4])([O-])=[O:2].[Na+].[Br:6][C:7]1[CH:14]=[CH:13][C:10]([CH:11]=[O:12])=[CH:9][CH:8]=1>S(=O)(=O)(O)O>[Br:6][C:7]1[CH:14]=[CH:13][C:10]([CH:11]=[O:12])=[CH:9][C:8]=1[N+:1]([O-:4])=[O:2]

Participants

4

Reactant 2

HCID 24268Sodium NitrateHCID 707414-Bromobenzaldehyde

Product 1

HCID 8087924-Bromo-3-nitrobenzaldehydeYield 95%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
10 °C

Procedure

A suspension of sodium nitrate (1.37 g, 16.2 mmol) in concentrated sulfuric acid(15 mL) was stirred at 10° C. until a homogeneous solution was obtained. The solution was treated with 4-bromobenzaldehyde (2.50 g, 13.5 mmol) in portionwise fashion over a 20 minute period. The mixture was poured onto ice (50 g) and the resulting pale yellow precipitate was collected by filteration. The precipitate was washed with copious amounts of water and then dried at 30° C. under reduced pressure to provide the title compound (2.95 g, 12.8 mmol, 95%) as a pale yellow solid. MS (DCI/NH3) m/e 229 (M+H)+.

Workup

  1. customwas obtained
  2. additionThe mixture was poured onto ice (50 g)
  3. customthe resulting pale yellow precipitate was collected by filteration
  4. washThe precipitate was washed with copious amounts of water
  5. customdried at 30° C. under reduced pressure

Sources & evidence

ORD record
ord-0a0dd137a9e64369b4bc59a2aaf9bbef
Source dataset
uspto-grants-2004_08
Patent number
US06780872B2

Reaction notes

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