Trimethylsilyl triflate → 1-[4-(Benzyloxy)phenyl]-2-bromoethan-1-one
Reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:17])[CH3:16])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[Si](OS(C(F)(F)F)(=O)=O)(C)(C)C.C1C(=O)N([Br:46])C(=O)C1>C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:15](=[O:17])[CH2:16][Br:46])=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Participants
6
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 1-(4-(benzyloxy)-phenyl)-ethanone (49.12 g; 217.1 mmol) in CH2Cl2 (750 mL) was added drop wise DIPEA (45.37 mL; 260.5 mmol) and TMSOTf (45.18 mL; 249.6 mmol), both at 0° C. The resulting solution was maintained at 0° C. for 1 h, and then NBS (42.50 g; 238.8 mmol) was added in four portions. The resulting mixture was allowed to warm to RT and stirred 1 hour. Subsequently, the mixture was concentrated in vacuo and the residue was treated with EtOAc and washed twice with water, and brine. The organic layer was dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by column chromatography (SiO2, Et2O) and crystallization from iPr2O to afford 1-(4-benzyloxy-phenyl)-2-bromo-ethanone.
Workup
- customat 0° C
- temperatureto warm to RT
- concentrationSubsequently, the mixture was concentrated in vacuo
- additionthe residue was treated with EtOAc
- washwashed twice with water, and brine
- dry with materialThe organic layer was dried (MgSO4)
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe residue was purified by column chromatography (SiO2, Et2O) and crystallization from iPr2O
Sources & evidence
- ORD record
- ord-91b067787555423996a6a0dc5f41d985
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09227960B2
Reaction notes
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