Dimethylformamide → 3-Chloro-5-methoxybenzaldehyde

HRID 1760036Notes

Reaction equation

HRID 1760036 reaction equation
Cl[C:2]1[CH:3]=[C:4]([O:9][CH3:10])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[Mg].C(Br)C.CN([CH:18]=[O:19])C>C1COCC1>[CH3:10][O:9][C:4]1[CH:3]=[C:2]([CH:7]=[C:6]([Cl:8])[CH:5]=1)[CH:18]=[O:19]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6332Ethyl BromideHCID 365883,5-DichloroanisoleHCID 5462224Magnesium

Product 1

HCID 219046333-Chloro-5-methoxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

3,5-Dichloroanisol (1.1 g; 6.8 mmol) was added in portions to magnesium chips (0.20 g; 8.2 mmol) in THF (dry, 20 mL). After the first addition, EtBr (0.1 mL) was added to start the reaction. After total addition the reaction mixture was stirred at 60° C. overnight, whereafter the mixture was cooled to 0° C., and DMF was added. After stirring for 1 hour, the mixture was poured onto HCl/aq, concentrated, and extracted with ether (3×50 mL). The combined organic phase was washed with water, dried (Na2SO4), and concentrated, yielding 2.35 g of the sub-title compound.

Workup

  1. additionwas added
  2. customthe reaction
  3. additionAfter total addition the reaction mixture
  4. temperaturewas cooled to 0° C.
  5. stirringAfter stirring for 1 hour
  6. additionthe mixture was poured onto HCl/aq
  7. concentrationconcentrated
  8. extractionextracted with ether (3×50 mL)
  9. washThe combined organic phase was washed with water
  10. dry with materialdried (Na2SO4)
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-5e1289d32ceb493b80683eb3e4d5f654
Source dataset
uspto-grants-2005_01
Patent number
US06838478B2

Reaction notes

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