Sodium Bicarbonate → 4-Iodo-2-nitrobenzaldehyde

HRID 1686857Notes

Reaction equation

HRID 1686857 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-66183504377242d0bb32ec16048286eb
Source dataset
uspto-grants-2012_04
Patent number
US08148503B2

Reaction notes

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