Sodium Nitrate → 4-Bromo-3-nitrobenzaldehyde

HRID 1862439Notes

Reaction equation

HRID 1862439 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-dd930f87cb8242b18dbd1c12c9a3c83a
Source dataset
uspto-grants-2003_03
Patent number
US06538004B2

Reaction notes

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