Bromine → 5-bromo-3-tert-butyl-2-hydroxybenzaldehyde

HRID 1296019Notes

Reaction equation

HRID 1296019 reaction equation
[Br:1]Br.[C:3]([C:7]1[C:8]([O:15]COC)=[C:9]([CH:12]=[CH:13][CH:14]=1)[CH:10]=[O:11])([CH3:6])([CH3:5])[CH3:4]>CO>[Br:1][C:13]1[CH:14]=[C:7]([C:3]([CH3:6])([CH3:5])[CH3:4])[C:8]([OH:15])=[C:9]([CH:12]=1)[CH:10]=[O:11]

Participants

4

Reactant 2

HCID 24408BromineHCID 22930050HCID 22930050, compound

Product 1

HCID 7970065-bromo-3-tert-butyl-2-hydroxybenzaldehydeYield 111%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

Bromine (747 g) was gradually added to a solution of the 3-(tert-butyl)-2-(methoxymethoxy)benzaldehyde (1247 g, 4.67 mol) in methanol (4000 ml) while cooling on ice. After stirring at 20° C. for 1 hour, the solvent was distilled off under reduced pressure, ethyl acetate was added to the residue, the mixture was washed with water, saturated sodium aqueous hydrogencarbonate and brine in that order and the organic layer was dried over anhydrous magnesium sulfate. The organic layer was concentrated under reduced pressure to yield a crude product of the title compound (1333 g) as a red oil.

Workup

  1. temperaturewhile cooling on ice
  2. distillationthe solvent was distilled off under reduced pressure, ethyl acetate
  3. additionwas added to the residue
  4. washthe mixture was washed with water, saturated sodium aqueous hydrogencarbonate and brine in that order
  5. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  6. concentrationThe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-3b9cde35ea9f4b3fb439de6be3084343
Source dataset
uspto-grants-2007_07
Patent number
US07244730B2

Reaction notes

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