Sodium Bicarbonate → 4-Iodo-2-nitrobenzaldehyde

HRID 333460Notes

Reaction equation

HRID 333460 reaction equation
[C:1]([O-:4])(O)=O.[Na+].BrC[C:8]1[CH:13]=[CH:12][C:11]([I:14])=[CH:10][C:9]=1[N+:15]([O-:17])=[O:16]>CS(C)=O.O>[I:14][C:11]1[CH:12]=[CH:13][C:8]([CH:1]=[O:4])=[C:9]([N+:15]([O-:17])=[O:16])[CH:10]=1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 179660241-(Bromomethyl)-4-iodo-2-nitrobenzene

Product 1

HCID 215327854-Iodo-2-nitrobenzaldehydeYield 61%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
86 °C

Procedure

NaHCO3 (3.32 g, 39.48 mmol) was added to a solution of 1-bromomethyl-4-iodo-2-nitrobenzene (2.25 g, 6.58 mmol) in anhydrous DMSO (150 mL). The mixture was stirred at 86° C. for 19 hours under a nitrogen atmosphere, then cooled down to room temperature, diluted with water (300 mL), and extracted with methylene chloride four times (250 mL). The combined organic phase was dried over Na2SO4, concentrated in vacuo, and purified by silica gel chromatography to yield 4-iodo-2-nitrobenzaldehyde (1.11 g, 61%). 1H NMR (400 MHz, CDCl3): δ 10.38 (d, 1H, J=1.6 Hz, CHO), 8.45 (d, 1H, J=1.5 Hz, Ph-H), 8.15 (dd, 1H, J=1.5 and 8.0 Hz, Ph-H), 7.67 (d, 1H, J=8.1 Hz, Ph-H); 13C NMR (100 MHz, CDCl3): δ 187.28 (CH), 143.18 (CH), 133.29 (CH), 130.67 (CH), 130.28 (C), 109.60 (C), 99.78 (C).

Workup

  1. temperaturecooled down to room temperature
  2. extractionextracted with methylene chloride four times (250 mL)
  3. dry with materialThe combined organic phase was dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-1ebb7e0662fd4d42a6223b7b34fe5d78
Source dataset
uspto-grants-2014_11
Patent number
US08877905B2

Reaction notes

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