Bromoacetyl bromide → HCID 10946441, compound
Reaction equation
[CH2:1]1[O:6][C:4](=[O:5])[NH:3][CH:2]1[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[Li]CCCC.[Br:19][CH2:20][C:21](Br)=[O:22].CCOC(C)=O.CCCCCC>C1COCC1.C(OCC)(=O)C>[CH2:7]([C@H:2]1[CH2:1][O:6][C:4](=[O:5])[N:3]1[C:21](=[O:22])[CH2:20][Br:19])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1Participants
Conditions
- Temperature
- -78 °C
Procedure
To a solution of S-(−)-4-benzyl-2-oxazolidinone (20.0 g, 112.86 mmol) in THF (200 mL) was added nBuLi (2.5M in hexanes, 47.4 mL, 118.51 mmol) dropwise at −78° C. The solution was stirred at −78° C. for 30 min followed by the addition of bromo acetyl bromide (25.0 g, 10.81 mL, 124.15 mmol). The solution was allowed to warm to 25° C. overnight (19 h). An aliquot was taken and TLC (1:2 EtOAc-hexane) indicated that the reaction was complete. It was diluted with ethyl acetate (200 mL) and the organic layer was washed with saturated aqueous NaHCO3 (2×50 mL). The organic layer was dried over MgSO4, filtered and concentrated to obtain a crude brown oil (34 g). The crude product was purified by flash chromatography, eluent: 1:4 EtOAc-hexane, to furnish (4S)-4-benzyl-3-(bromoacetyl)-1,3-oxazolidin-2-one as a colorless oil (33.2 g, 98.6%). Mass Spectrum (−ESI): 297 (M−H)−.
Workup
- temperatureto warm to 25° C. overnight (19 h)
- washthe organic layer was washed with saturated aqueous NaHCO3 (2×50 mL)
- dry with materialThe organic layer was dried over MgSO4
- filtrationfiltered
- concentrationconcentrated
- customto obtain a crude brown oil (34 g)
- customThe crude product was purified by flash chromatography, eluent
Sources & evidence
- ORD record
- ord-8873ee11e98945458fb6cbec9c80caf0
- Source dataset
- uspto-grants-2010_12
- Patent number
- US07858658B2
Reaction notes
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