Hydrochloric Acid → (5-Bromo-2,3-dimethoxyphenyl)methanol

HRID 1296204Notes

Reaction equation

HRID 1296204 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([O:12][CH3:13])[C:5]([O:10][CH3:11])=[C:6]([CH:9]=1)[CH:7]=[O:8].[BH4-].[Na+].Cl>O1CCCC1.C(O)C>[Br:1][C:2]1[CH:3]=[C:4]([O:12][CH3:13])[C:5]([O:10][CH3:11])=[C:6]([CH:9]=1)[CH2:7][OH:8]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3224055-Bromo-2,3-dimethoxybenzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 2194090(5-Bromo-2,3-dimethoxyphenyl)methanolYield 95.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

10.67 g of 5-bromo-2,3-dimethoxybenzaldehyde was dissolved in 100 ml of tetrahydrofuran and 100 ml of ethanol, and 1 g of sodium borohydride was added, and then the solution was stirred overnight at room temperature. 1 N hydrochloric acid was added thereto, followed by extracting with ethyl acetate. The organic layer was washed with water and an aqueous saturated sodium chloride, dried over anhydrous magnesium sulfate and the solvent was evaporated, to give 10.27 g of 5-bromo-2,3-dimethoxybenzyl alcohol. 5.326 g of this crude product was dissolved in 50 ml of N,N-dimethylformamide, and 1.8 g of imidazole and 5.9 g of t-butylchlorodiphenylsilane were added thereto, and the solution was stirred overnight at room temperature. The reaction mixture was diluted with ethyl acetate, and the organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and the solvent was evaporated, to give 10.72 g of [(5-bromo-2,3-dimethoxybenzyl)oxy](t-butyl)diphenylsilane.

Workup

  1. extractionby extracting with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialan aqueous saturated sodium chloride, dried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-7f4299c661c64149a844fba7d3690b01
Source dataset
uspto-grants-2007_07
Patent number
US07244861B2

Reaction notes

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