2-Bromopropane → 3-Bromo-4-(propan-2-yloxy)benzaldehyde

HRID 1107295Notes

Reaction equation

HRID 1107295 reaction equation
C(=O)([O-])[O-].[K+].[K+].Br[CH:8]([CH3:10])[CH3:9].[Br:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][C:19]=1[OH:20])[CH:15]=[O:16]>CN(C)C=O>[Br:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][C:19]=1[O:20][CH:8]([CH3:10])[CH3:9])[CH:15]=[O:16]

Participants

5

Reactant 3

HCID 63582-BromopropaneHCID 11430Potassium CarbonateHCID 763083-Bromo-4-hydroxybenzaldehyde

Product 1

HCID 38328433-Bromo-4-(propan-2-yloxy)benzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (10.28 g, 7.4 mmol) and 2-bromopropane (8.7 ml) were added to 3-bromo-4-hydroxybenzaldehyde (7.46 g, 3.7 mmol) in N,N-dimethylformamide (20 ml). The mixture was stirred at room temperature for 3 hours, then partitioned between ethyl acetate and water. The organic phase was washed with brine and dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with hexane/EtOAc (90:10 increasing to 80:20) to give the title compound (5.34 g). 1H NMR (250 MHz, CDCl3) δ 9.82 (1H, s), 8.03 (1H, d, J=2.0 Hz), 7.82-7.78 (1H, dd, J=6.0, 2.0 Hz), 7.00 (1H, d, J=6.0 Hz), 4.72 (1H, septet, J=6.0 Hz), and 1.40 (6H, d, J=6.0 Hz).

Workup

  1. custompartitioned between ethyl acetate and water
  2. washThe organic phase was washed with brine
  3. dry with materialdried (MgSO4)
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by flash column chromatography on silica gel
  6. washeluting with hexane/EtOAc (90:10 increasing to 80:20)

Sources & evidence

ORD record
ord-128532d5d3db439688761b6d61c399a4
Source dataset
uspto-grants-2000_05
Patent number
US06060469

Reaction notes

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