Potassium Iodide → 3-Bromo-4-(propan-2-yloxy)benzaldehyde
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[CH:5]=[O:6].C(=O)([O-])[O-].[K+].[K+].[I-].[K+].Br[CH:20]([CH3:22])[CH3:21]>C(OCC)(=O)C.CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH:20]([CH3:22])[CH3:21])[CH:5]=[O:6]Participants
7
Procedure
To a mixture of 3-bromo-4-hydroxybenzaldehyde (2.5 g, 12.4 mmol), potassium carbonate (2.57 g, 18.6 mmol), potassium iodide (0.21 g, 1.24 mmol) and N,N-dimethylformamide (30 mL) was added 2-bromopropane (1.46 mL, 15.5 mmol) under stirring at room temperature, and the mixture was stirred at 70° C. for 18 hr. The reaction mixture was diluted with ethyl acetate, washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated. under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-3/1) to give the title compound (1.77 g, yield 59%) as a pale-yellow oil.
Workup
- stirringthe mixture was stirred at 70° C. for 18 hr
- washwashed with water and saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated
- customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-3/1)
Sources & evidence
- ORD record
- ord-41fd4abfc4d8430aad3fccdc16b0e393
- Source dataset
- uspto-grants-2010_08
- Patent number
- US07786165B2
Reaction notes
Loading…