Sodium hydride → 1-Bromo-methoxy-2-methoxymethoxybenzene

HRID 650409Notes

Reaction equation

HRID 650409 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5](OC)=[CH:4][C:3]=1[O:10][CH2:11][O:12][CH3:13].[H-].[Na+].BrC1C=CC(OC)=CC=1O.C[O:27][CH2:28][Br:29]>CN(C=O)C>[Br:29][CH2:28][O:27][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:10][CH2:11][O:12][CH3:13]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 83093Bromomethyl methyl etherHCID 134938392-Bromo-5-methoxyphenolHCID 148270371-Bromo-4-methoxy-2-(methoxymethoxy)benzene

Product 1

HCID 702343071-Bromo-methoxy-2-methoxymethoxybenzeneYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-Bromo-4-methoxy-2-methoxymethoxybenzene. To a suspension of NaH (2.5 g, 0.06 mol) in dry DMF (100 mL) at 0° C. was added solution of 1-bromo-2-hydroxy-4-methoxybenzene (10.6 g, 0.05 mol). After stirring at 0° C. for 30 min. bromomethyl methyl ether (7.8 g, 0.06 mmol) were dropwise added. The mixture was warmed to room temperature over 20 min. and then stirred for 2 h, it was then quenched cautiously by the addition of cold dilute HCl and extracted with EtOAc. The EtOAc extract was washed successively with; H2O, 5% aqueous NaHCO3, H2O and finally brine. After drying (MgSO4) filtration and evaporation gave liquids. The product was purified by distillation (85° C., 0.2 mm Hg) to give the title compound as a colorless oil (13.7 g, 97%).

Workup

  1. additionwere dropwise added
  2. customit was then quenched cautiously by the addition of cold dilute HCl
  3. extractionextracted with EtOAc
  4. extractionThe EtOAc extract
  5. washwas washed successively with
  6. customAfter drying
  7. filtration(MgSO4) filtration and evaporation
  8. customgave liquids
  9. distillationThe product was purified by distillation (85° C., 0.2 mm Hg)

Sources & evidence

ORD record
ord-b9add953ea2b4ac880354c120c507f37
Source dataset
uspto-grants-2001_08
Patent number
US06271399B1

Reaction notes

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