1-Bromo-2-methylpropane → 5-bromo-2-isobutoxybenzaldehyde

HRID 1245835Notes

Reaction equation

HRID 1245835 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].C(=O)([O-])[O-].[K+].[K+].Br[CH2:18][CH:19]([CH3:21])[CH3:20]>CN(C)C=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:18][CH:19]([CH3:21])[CH3:20])=[C:6]([CH:9]=1)[CH:7]=[O:8]

Participants

5

Reactant 3

HCID 65551-Bromo-2-methylpropaneHCID 11430Potassium CarbonateHCID 728635-Bromosalicylaldehyde

Product 1

HCID 9750405-bromo-2-isobutoxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 5-bromo-2-hydroxybenzaldehyde (7.63 g) in dimethylformamide (40 ml) was added anhydrous potassium carbonate (15.7 g) followed by 1-bromo-2-methylpropane (6.2 ml). The resulting mixture was heated to 70° C. for 18 h. The mixture was partitioned between water and ethyl acetate. The organic layer was washed with 2N sodium hydroxide, dried (MgSO4) and evaporated to give an oil which was purified by column chromatography eluting with ethyl acetate/iso-hexane (10:90) to give 5-bromo-2-isobutoxybenzaldehyde (9.52 g) as an oil.

Workup

  1. customThe mixture was partitioned between water and ethyl acetate
  2. washThe organic layer was washed with 2N sodium hydroxide
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customto give an oil which
  6. customwas purified by column chromatography
  7. washeluting with ethyl acetate/iso-hexane (10:90)

Sources & evidence

ORD record
ord-b4d66dfcb5f745399dd1b0a9d9a8e87c
Source dataset
uspto-grants-2006_10
Patent number
US07125896B2

Reaction notes

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