Sodium Bicarbonate → 4-Methoxy-2-nitrobenzaldehyde

HRID 1914693

Reaction equation

HRID 1914693 reaction equation
Br[CH:2](Br)[C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[N+:11]([O-:13])=[O:12].C([O-])(O)=[O:16].[Na+]>O>[CH3:10][O:9][C:6]1[CH:7]=[CH:8][C:3]([CH:2]=[O:16])=[C:4]([N+:11]([O-:13])=[O:12])[CH:5]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 35023351-(Dibromomethyl)-4-methoxy-2-nitrobenzene

Product 1

HCID 3576914-Methoxy-2-nitrobenzaldehydeYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1-(dibromomethyl)-4-methoxy-2-nitrobenzene (42 g, 0.23 mol) and NaHCO3 (3 Eq) in water (400 mL) is refluxed for 22 h. The reaction mixture is cooled to room temperature and the product is extracted with EtOAc (2×150 mL). The organic layer is washed with a solution of 1.5N HCl (2×100 mL), water (2×100 mL) and brine then dried over Na2SO4. The solvent is removed under reduced pressure to afford 20 g (85%) of the title compound as a brown solid. 1H NMR (DMSO-d6, 400 MHz) δ 10.03 (s, 1H), 7.93-7.95 (m, 1H), 7.61 (s, 1H), 7.40-7.41 (m, 1H), 3.93 (s, 3H).

Workup

  1. temperatureis refluxed for 22 h
  2. extractionthe product is extracted with EtOAc (2×150 mL)
  3. washThe organic layer is washed with a solution of 1.5N HCl (2×100 mL), water (2×100 mL) and brine
  4. dry with materialthen dried over Na2SO4
  5. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-810510ceaf56408aadd3a32e6869fdf2
Source dataset
uspto-grants-2013_12
Patent number
US08614215B2

Linked notes

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