Hydrochloric Acid → 4-Bromo-1-methoxy-2-(2-methoxy-ethoxymethyl)-benzene

HRID 1158467Notes

Reaction equation

HRID 1158467 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH3:11])=[C:6]([CH2:8][OH:9])[CH:7]=1.[CH3:12][O:13][CH2:14][CH2:15]Br.[H-].[Na+].Cl>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH3:11])=[C:6]([CH2:8][O:9][CH2:15][CH2:14][O:13][CH3:12])[CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 809722-Bromoethyl methyl etherHCID 6122985-Bromo-2-methoxybenzyl alcohol

Product 1

HCID 615316034-Bromo-1-methoxy-2-(2-methoxy-ethoxymethyl)-benzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (5-bromo-2-methoxy-phenyl)-methanol (3.38 g, 14.8 mmol) and 2-bromoethyl methyl ether (2.06 g, 14.8 mmol) in DMF (30 mL) is added NaH (55% dispersion in oil; 1.36 g, 31.1 mmol) in three portions at room temperature, followed by stirring overnight. The mixture is poured into ice-cooled aqueous 2N HCl, the water phase is extracted with diethyl ether, the combined organic phase is washed with brine, dried (Na2SO4) and concentrated. Purification by flash chromatography (hexane/AcOEt 3:1) gives the title compound as liquid. TLC, Rf (hexane/AcOEt 1:1)=0.44. 1H-NMR (CDCl3): δ 3.45 (s, 3H), 3.64 (m, 2H), 3.71 (m, 2H), 3.83 (s, 3H), 4.60 (s, 2H), 6.76 (d, 1H), 7.37 (dd, 1H), 7.56 (d, 1H) ppm.

Workup

  1. additionThe mixture is poured into ice-
  2. extractionthe water phase is extracted with diethyl ether
  3. washthe combined organic phase is washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customPurification by flash chromatography (hexane/AcOEt 3:1)

Sources & evidence

ORD record
ord-478f5692f25a4bc594d39abd9896b79a
Source dataset
uspto-grants-2010_10
Patent number
US07807709B2

Reaction notes

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