4-Iododibenzofuran → 4-Cyclohexyldibenzo[b,d]furan

HRID 929278Notes

Reaction equation

HRID 929278 reaction equation
[CH:1]1([Mg]Cl)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.I[C:10]1[C:15]2[O:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[C:14]=2[CH:13]=[CH:12][CH:11]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1>[Cl-].[Cl-].[Zn+2].C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1COCC1>[CH:1]1([C:22]2[C:17]3[O:16][C:15]4[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=4[C:18]=3[CH:19]=[CH:20][CH:21]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 3

HCID 4582574-IododibenzofuranHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 178478990HCID 178478990, compound

Product 1

HCID 1178939144-Cyclohexyldibenzo[b,d]furanYield 90%

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

ZnCl2 (13.6 g, 100.0 mmol) and THF (600 mL) were cooled to 0° C. After that, cyclohexylmagnesium chloride (70.0 mL, 70.0 mmol, 1M in THF) was added at 0° C. The mixture was stirred for 15 min from 0° C. to room temperature. The mixture was bubbled with nitrogen for 15 min, followed by the addition of 4-iododibenzo[b,d]furan (11.8 g, 40.0 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (3.3 g, 8.0 mmol), and Pd2(dba)3 (1.8 g, 2.0 mmol). The resultant mixture was bubbled with nitrogen for 15 min and stirred for 48 h. The reaction mixture was quenched by the addition of saturated K2CO3 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 10% DCM/hexane to yield 4-cyclohexyldibenzo[b,d]furan (9.0 g, 90% yield) as a colorless oil.

Workup

  1. customThe mixture was bubbled with nitrogen for 15 min
  2. customThe resultant mixture was bubbled with nitrogen for 15 min
  3. stirringstirred for 48 h
  4. customThe reaction mixture was quenched by the addition of saturated K2CO3 solution
  5. extractionextracted with DCM
  6. dry with materialThe extracts were dried over MgSO4
  7. customthe solvent was removed in vacuo
  8. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-9d3762a955ea4db1873138b3f8da8374
Source dataset
uspto-grants-2016_03
Patent number
US09293712B2

Reaction notes

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