Methyl iodide → 1-Bromo-4-(1-methoxycyclobutyl)benzene
Reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2([OH:14])[CH2:13][CH2:12][CH2:11]2)=[CH:6][CH:5]=1.[CH3:15]I>CN(C=O)C>[Br:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2([O:14][CH3:15])[CH2:13][CH2:12][CH2:11]2)=[CH:8][CH:9]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a suspension of NaH (24 mg, ˜55% dispersion in oil, 0.53 mmol) in DMF (2 ml) at 0° C. was added a solution of 1-(4-bromophenyl)-cyclobutanol (100 mg, 0.44 mmol) in DMF (2 ml). The mixture was stirred at 0° C. for 30 min and then methyl iodide (41 μl, 0.66 mmol) was added. The reaction mixture was then warmed up to rt and stirring was continued overnight. The mixture was quenched with water and extracted with ether. The organic phase was washed with water and brine, dried (MgSO4), filtered, and concentrated in vacuo to give a residue which was purified by flash column chromatography (1:9 ether:pentane) to give 1-bromo-4-(1-methoxycyclobutyl)-benzene (79 mg, 75%) as a colorless oil. 1H NMR (CDCl3, 300 MHz): δ 7.50 (d, J=8.5 Hz, 2H), 7.30 (d, J=8.5 Hz, 2H), 2.92 (s, 3H), 2.38-2.33 (m, 4H), 1.94 (m, 1H), 1.67 (m, 1H).
Workup
- temperatureThe reaction mixture was then warmed up to rt
- stirringstirring
- waitwas continued overnight
- customThe mixture was quenched with water
- extractionextracted with ether
- washThe organic phase was washed with water and brine
- dry with materialdried (MgSO4)
- filtrationfiltered
- concentrationconcentrated in vacuo
- customto give a residue which
- customwas purified by flash column chromatography (1:9 ether:pentane)
Sources & evidence
- ORD record
- ord-23235164c34e46c28dc6a71072bb381c
- Source dataset
- uspto-grants-2007_08
- Patent number
- US07259183B2
Reaction notes
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