Methyl iodide → HCID 274359, compound

HRID 1247699Notes

Reaction equation

Br[C:2]1([Br:17])[CH2:4][C:3]1([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH2:18]([Li])CCC.CCCCCC.CI>O.C1COCC1>[Br:17][C:2]1([CH3:18])[CH2:4][C:3]1([C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

Conditions

Temperature: -70 °C

Procedure

Under a nitrogen atmosphere, 1,1-dibromo-2,2-diphenylcyclopropane(10.6 g, 30.0 mmol) obtained in Example 1-(1) and THF (tetrahydrofuran, 120 ml) were placed in a reaction flask and cooled to −70° C. To the mixture, n-butyllithium in hexane (20 ml, 1.57M, 31.4 mmol) was added gradually, and the mixture was stirred at the same temperature for 30 minutes. Methyl iodide (2.1 ml, 33 mmol) was added to the reaction mixture and the resulting mixture was stirred for 30 minutes and then warmed to room temperature. Then, water was added to the reaction mixture and the organic layer was extracted with toluene. The toluene extract was dried over anhydrous magnesium sulfate and then the solvent was removed under reduced pressure. The residue was recrystallized from methanol to give the title compound (7.28 g, 89%) as white crystal.

Workup

stirringthe resulting mixture was stirred for 30 minutes
temperaturewarmed to room temperature
extractionthe organic layer was extracted with toluene
extractionThe toluene extract
dry with materialwas dried over anhydrous magnesium sulfate
customthe solvent was removed under reduced pressure
customThe residue was recrystallized from methanol

Sources & evidence

ORD record: ord-925d27d2d84d48f3850e1408e563b9ed
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07129367B2

Reaction notes

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