Bromine → 5-Bromo-2-isopropylbenzaldehyde
Reaction equation
[CH:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH:6]=[O:7])([CH3:3])[CH3:2].[Al+3].[Cl-].[Cl-].[Cl-].[Br:16]Br.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[Br:16][C:9]1[CH:10]=[CH:11][C:4]([CH:1]([CH3:3])[CH3:2])=[C:5]([CH:8]=1)[CH:6]=[O:7]Participants
6
Conditions
- Temperature
- 0 °C
Procedure
A solution of 2-isopropyl benzaldehyde (1.5 g, 10.13 mmole) in DCM (10 mL) was added to a solution of AlCl3 (2.6 g, 20.26 mmole) in DCM (10 mL) at 0° C. followed by addition of a dilute solution of Br2 (0.67 mL, 13.1 mmole in 20 mL DCM) to the reaction mixture. The solution was stirred at 0° C. for 6 hours then stirred overnight at room temperature. The reaction mixture was basified using saturated aqueous sodium bicarbonate and extracted with DCM (30×2 mL). The organic layers were combined and the crude product was obtained by evaporation of the solvent. The crude product was purified by column chromatography using 1% EtOAc in Hexane to yield 5-bromo-2-isopropylbenzaldehyde (800 mg).
Workup
- stirringthen stirred overnight at room temperature
- extractionextracted with DCM (30×2 mL)
- customthe crude product was obtained by evaporation of the solvent
- customThe crude product was purified by column chromatography
Sources & evidence
- ORD record
- ord-457bdfb0c3af4d119e147c15dc2dc18d
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08828951B2
Reaction notes
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