Isopropanol → 2-Bromo-5-(isopropoxymethyl)-1,3-dimethoxybenzene

HRID 41246Notes

Reaction equation

HRID 41246 reaction equation
CN(C)C=O.[CH3:6][CH:7]([OH:9])[CH3:8].[H-].[Na+].[Br:12][C:13]1[C:18]([O:19][CH3:20])=[CH:17][C:16]([CH2:21]Cl)=[CH:15][C:14]=1[O:23][CH3:24]>O>[Br:12][C:13]1[C:18]([O:19][CH3:20])=[CH:17][C:16]([CH2:21][O:9][CH:7]([CH3:8])[CH3:6])=[CH:15][C:14]=1[O:23][CH3:24]

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 6228Dimethylformamide2×HCID 24758Sodium hydrideHCID 249719722-Bromo-5-(chloromethyl)-1,3-dimethoxybenzene

Product 1

HCID 582234542-Bromo-5-(isopropoxymethyl)-1,3-dimethoxybenzeneYield 62.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To an N,N-dimethylformamide (15 ml) solution of 2-propanol (7.81 ml, 102 mmol) was added sodium hydride (4.08 g, 102 mmol) at room temperature, and the mixture was stirred for 30 minutes. To the mixture was added an N,N-dimethylformamide (15 ml) solution of 2-bromo-5-(chloromethyl)-1,3-dimethoxybenzene (2.70 g, 10.2 mmol) and the mixture was stirred for one hour. After the reaction was completed, water was added to the reaction mixture while cooling on ice, which was extracted with ethyl acetate and dried over anhydrous magnesium sulfate, and the solvent was then distilled off under reduced pressure. The residue was purified by silica gel column chromatography (n-heptane/ethyl acetate: 3/1) to obtain the title compound (1.85 g, 6.40 mmol).

Workup

  1. stirringthe mixture was stirred for one hour
  2. temperaturewhile cooling on ice, which
  3. extractionwas extracted with ethyl acetate
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was then distilled off under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (n-heptane/ethyl acetate: 3/1)

Sources & evidence

ORD record
ord-b0a3d06e3a164d8787bcb50a31dd6478
Source dataset
uspto-grants-2013_09
Patent number
US08530504B2

Reaction notes

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