2-Bromo-4-tert-butylbenzaldehyde → HCID 20382954, compound
Reaction equation
[CH2:1]([Li])CCC.[Br:6][C:7]1[CH:14]=[C:13]([C:15]([CH3:18])([CH3:17])[CH3:16])[CH:12]=[CH:11][C:8]=1[CH:9]=O>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[Br:6][C:7]1[CH:14]=[C:13]([C:15]([CH3:18])([CH3:17])[CH3:16])[CH:12]=[CH:11][C:8]=1[CH:9]=[CH2:1]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
To a stirred suspension of methyltriphenylphosphonium bromide (12.3 g, 33.7 mmol) in anhydrous THF (40 ml) was added n-butyl lithium (1.60 mol/l, hexane solution) (33.7 mmol, 21.1 ml) at 0° C. After 30 minutes at 0° C., to this was added 2-bromo-4-tert-butylbenzaldehyde (4.06 g, 16.8 mmol)(prepared according to J. Med. Chem. 2005, 48, 71-90) in anhydrous THF (10 ml) at 0° C. The reaction mixture was stirred at ambient temperature for 3 hours. The mixture was quenched with saturated ammonium chloride solution and extracted with EtOAc. The combined solution was washed with brine, dried over sodium sulfate and concentrated in vacuo to give the crude product. The crude product was purified by column chromatography on silica gel, eluting with hexane, to afford the title compound (3.27 g, 81%) as a colorless oil.
Workup
- customThe mixture was quenched with saturated ammonium chloride solution
- extractionextracted with EtOAc
- washThe combined solution was washed with brine
- dry with materialdried over sodium sulfate
- concentrationconcentrated in vacuo
- customto give the crude product
- customThe crude product was purified by column chromatography on silica gel
- washeluting with hexane
Sources & evidence
- ORD record
- ord-07c7565ee8124b8db930fefbc750e56f
- Source dataset
- uspto-grants-2009_11
- Patent number
- US07622589B2
Reaction notes
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