Iodine → 4-Cyclohexyl-6-iododibenzo[b,d]furan

HRID 929279Notes

Reaction equation

[CH:1]1([C:7]2[C:12]3[O:13][C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=4[C:11]=3[CH:10]=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Li]CCCC.[I:25]I>C1COCC1>[CH:1]1([C:7]2[C:12]3[O:13][C:14]4[C:19]([I:25])=[CH:18][CH:17]=[CH:16][C:15]=4[C:11]=3[CH:10]=[CH:9][CH:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

Conditions

Temperature: -90 °C

Procedure

4-Cyclohexyldibenzo[b,d]furan (11.3 g, 45.0 mmol) and THF (1000 mL) were cooled down to −90° C. After that, n-BuLi (56.2 mL, 90.0 mmol, 1.6 M in THF) was added at −90° C. The mixture was stirred for 6 h and allowed to warm from −90° C. to room temperature. The mixture was then cooled to −90° C., and iodine (22.9 g, 90.0 mmol) was added at −90° C. The resultant mixture was stirred for 17 h and allowed to warm from −90° C. to room temperature. The reaction mixture was then quenched by the addition of saturated Na2S2O3 solution and extracted with DCM. The extracts were dried over MgSO4 and the solvent was removed in vacuo. The residue was purified by flash chromatography using 5% DCM/hexane to yield 4-cyclohexyl-6-iododibenzo[b,d]furan (9.8 g, 58% yield) as a white solid.

Workup

temperatureto warm from −90° C. to room temperature
temperatureto warm from −90° C. to room temperature
customThe reaction mixture was then quenched by the addition of saturated Na2S2O3 solution
extractionextracted with DCM
dry with materialThe extracts were dried over MgSO4
customthe solvent was removed in vacuo
customThe residue was purified by flash chromatography

Sources & evidence

ORD record: ord-29b961f37fd140f4a11aabb9503d1bad
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09293712B2

Reaction notes

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