Isopropanol → 1,3-DibroMo-5-isopropoxybenzene
Reaction equation
[H-].[Na+].[CH3:3][CH:4]([OH:6])[CH3:5].[Br:7][C:8]1[CH:13]=[C:12](F)[CH:11]=[C:10]([Br:15])[CH:9]=1.C([O-])(O)=O.[Na+]>CN(C=O)C>[Br:7][C:8]1[CH:13]=[C:12]([O:6][CH:4]([CH3:5])[CH3:3])[CH:11]=[C:10]([Br:15])[CH:9]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of NaH 60% dispersion in mineral oil (1.89 g, 47.25 mmol) in dry DMF (20 mL) under inert atmosphere was added dropwise at 0° C. i-PrOH (3.62 mL, 47.25 mmol). The mixture was stirred at 0° C. for 15 min. Then, a solution of 1,3-dibromo-5-fluoro-benzene (1.98 mL, 15.75 mmol) in dry DMF (20 mL) was added dropwise at 0° C. The reaction mixture was stirred for 16 h at room temperature. A saturated solution of NaHCO3 was added dropwise and the crude product was extracted with Et2O (2 times), the organic layer was washed with a saturated solution of NaHCO3 (3 times), then with a saturated solution of NaCl, dried over MgSO4 and concentrated to give I-a as yellow oil in quantitative yield. 1H RMN (300 MHz, CDCl3) δ 7.21 (t, J=1.4 Hz, 1H), 6.97 (d, J=1.5 Hz, 2H), 4.61-4.40 (m, 1H), 1.32 (d, J=6.0 Hz, 6H).
Workup
- stirringThe reaction mixture was stirred for 16 h at room temperature
- extractionthe crude product was extracted with Et2O (2 times)
- washthe organic layer was washed with a saturated solution of NaHCO3 (3 times)
- dry with materialwith a saturated solution of NaCl, dried over MgSO4
- concentrationconcentrated
- customto give I-a as yellow oil in quantitative yield
Sources & evidence
- ORD record
- ord-21972f2f5fc343ef92c55ddc18c2ea49
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09168245B2
Reaction notes
Loading…