Hydrochloric Acid → 4-Bromo-2-(hydroxymethyl)-6-methoxyphenol

HRID 1698650

Reaction equation

HRID 1698650 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([O:11][CH3:12])[C:5]([OH:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].C1COCC1.[BH4-].[Na+].Cl>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]([O:11][CH3:12])[C:5]([OH:10])=[C:6]([CH2:7][OH:8])[CH:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 2622385-Bromo-2-hydroxy-3-methoxybenzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 8940924-Bromo-2-(hydroxymethyl)-6-methoxyphenolYield 99.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 50 g of 5-bromo-2-hydroxy-3-methoxybenzaldehyde in 200 ml of an ethanol:THF=1:1 mixed solvent there was added 16.4 g of sodium borohydride while cooling on ice. After stirring at room temperature for 2 hours, 1N hydrochloric acid was added to the reaction mixture while cooling on ice. The organic layer was washed with ethyl acetate and dried over anhydrous magnesium sulfate. The desiccating agent was filtered off, and the filtrate was concentrated under reduced pressure to give the title compound (50 g) as a crude product.

Workup

  1. temperaturewhile cooling on ice
  2. temperaturewhile cooling on ice
  3. washThe organic layer was washed with ethyl acetate
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationThe desiccating agent was filtered off
  6. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-4d7565a83e4d4822bdc6a69219ba005d
Source dataset
uspto-grants-2012_04
Patent number
US08163787B2

Linked notes

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