Imidazole → HCID 11659787, compound
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([Cl:9])[CH:3]=1.[Si:10](Cl)([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11].N1C=CN=C1>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][Si:10]([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11])=[C:4]([Cl:9])[CH:3]=1Participants
4
Procedure
4-bromo-2-chlorophenol (1.0 g, 4.82 mmol) was dissolved in MC (30 ml), followed by addition of tert-butyldimethylsilyl chloride (1.09 g, 7.23 mmol) and imidazole (492 mg, 7.23 mmol), and then the resulting mixture was stirred at room temperature under nitrogen stream for 24 hours. The resulting reaction liquid was sequentially washed with distilled water (15 ml) and a saturated aqueous NaHCO3 solution (15 ml), and then dried over anhydrous magnesium sulfate, followed by filtration and concentration. The residue thus obtained was subjected to MPLC (5% EtOAc/Hexanes), to obtain 1.69 g of colorless oil (99%).
Workup
- customThe resulting reaction liquid
- washwas sequentially washed with distilled water (15 ml)
- dry with materiala saturated aqueous NaHCO3 solution (15 ml), and then dried over anhydrous magnesium sulfate
- filtrationfollowed by filtration and concentration
- customThe residue thus obtained
Sources & evidence
- ORD record
- ord-7bc9d15b6a0d4df99ffe0eda68622dfa
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09096571B2
Reaction notes
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