Methyl iodide → 1-Bromo-4-(1-methoxycyclobutyl)benzene

HRID 2244313Notes

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]=1

Participants

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, described in example S2-A) 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 colourless oil. 1HNMR (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-04c8b04097394331bc98d747726beaef
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07678818B2

Reaction notes

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