Iodine → HCID 86700955, compound

HRID 713594Notes

Reaction equation

HRID 713594 reaction equation
[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[O:6][C:5]=2[C:4]([Si:14]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:3][CH:2]=1.C(=O)=O.CC(O)C.C([Li])CCC.CCCCCC.[I:51]I>C1COCC1.CCOCC>[I:51][C:13]1[C:7]2[O:6][C:5]3[C:4]([Si:14]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)([C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=4)[C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)=[CH:3][CH:2]=[CH:1][C:9]=3[C:8]=2[CH:10]=[CH:11][CH:12]=1

Participants

8

Reactant 5

HCID 807IodineHCID 8058HexaneHCID 5084353dibenzofuran-4-yl(triphenyl)silaneHCID 86586944Isopropanol carbon dioxide2×HCID 178418339Butyllithium

Product 1

HCID 86700955HCID 86700955, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Dibenzo[b,d]furan-4-yltriphenylsilane (9.80 g, 22.97 mmol) was dissolved in dry THF (100 mL) and cooled in the CO2/i-PrOH bath. n-Butyllithium in hexane (2.5 M, 12.87 mL, 32.2 mmol) was added dropwise. It was warmed to room temperature, stirred for 4 hours, and cooled again in the CO2/i-PrOH bath, and a solution of I2 (8.63 g, 34 mmol) in ether (50 mL) was added dropwise. The reaction mixture was warmed to room temperature, stirred for 1 hour, and quenched with an aqueous solution of NaHSO3 (10 wt %, 100 ml). It was diluted with saturated aqueous NaCl solution, extracted with EtOAc (50 mL×3 times). The organic extracts were combined, dried over anhydrous Na2SO4, and the solvent was evaporated. The residue was purified by column chromatography on silica gel with hexane/EtOAc (95/5 to 90/10, v/v) as eluent to yield (6-iododibenzo[b,d]furan-4-yl)triphenylsilane (7.8 g, 62%) as a white solid.

Workup

  1. temperatureThe reaction mixture was warmed to room temperature
  2. stirringstirred for 1 hour
  3. customquenched with an aqueous solution of NaHSO3 (10 wt %, 100 ml)
  4. additionIt was diluted with saturated aqueous NaCl solution
  5. extractionextracted with EtOAc (50 mL×3 times)
  6. dry with materialdried over anhydrous Na2SO4
  7. customthe solvent was evaporated
  8. customThe residue was purified by column chromatography on silica gel with hexane/EtOAc (95/5 to 90/10

Sources & evidence

ORD record
ord-3f732853da284c5eaee2b8612327cc29
Source dataset
uspto-grants-2015_11
Patent number
US09184399B2

Reaction notes

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