Acetone → 2-(6-Bromopyridin-2-yl)propan-2-ol
Reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[N:3]=1.[Li]CCCC.[CH3:14][C:15]([CH3:17])=[O:16]>CCOCC>[Br:8][C:4]1[N:3]=[C:2]([C:15]([OH:16])([CH3:17])[CH3:14])[CH:7]=[CH:6][CH:5]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
To a suspension of 2,6-dibromopyridine (1.0 eq.) in Et2O (0.2M) at −78° C. was added dropwise n-BuLi (1.05 eq.). The mixture was stirred at −78° C. for 45 min then acetone (1.5 eq.) was added. The final mixture was stirred for an extra 15 min at −78° C. and quenched with saturated aqueous NaHCO3. The mixture was extracted with EtOAc (2×). The combined organic extracts were washed with, brine, dried over MgSO4, filtered and concentrated to afford the title compound as a white solid which was used as such.
Workup
- customquenched with saturated aqueous NaHCO3
- extractionThe mixture was extracted with EtOAc (2×)
- washThe combined organic extracts were washed with, brine
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-fa1efcff9d0f45a7aead97cf5c3090fd
- Source dataset
- uspto-grants-2006_12
- Patent number
- US07153968B2
Reaction notes
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