1,2-Dimethoxyethane → HCID 69287869, compound

HRID 2373125Notes

Reaction equation

HRID 2373125 reaction equation
[C:1]1(B(O)O)[CH:6]=[CH:5][C:4](B(O)O)=[CH:3][CH:2]=1.I[C:14]1[CH:26]=[CH:25][C:17]([C:18]([O:20][CH2:21][CH2:22][CH2:23][CH3:24])=[O:19])=[CH:16][CH:15]=1.[C:27](=[O:30])([O-])[O-:28].[Na+].[Na+].CO[CH2:35][CH2:36]OC>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O.ClCCl.C(O)C>[C:1]1([C:14]2[C:26]([C:36]3[CH:35]=[CH:16][CH:15]=[CH:14][CH:26]=3)=[CH:25][C:17]([C:18]([O:20][CH2:21][CH2:22][CH2:23][CH3:24])=[O:19])=[CH:16][CH:15]=2)[CH:6]=[CH:5][C:4]([C:27]([O:28][CH2:21][CH2:22][CH2:23][CH3:24])=[O:30])=[CH:3][CH:2]=1

Participants

9

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 2304781,4-Benzenediboronic acidHCID 69285276HCID 69285276, compound

Product 1

HCID 69287869HCID 69287869, compound

Reagents, catalysts & solvents 4

HCID 178418476HCID 178418476, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Procedure

Finally, dibutyl 4,4′-terphenyl dicarboxylate (CS-13) was prepared. A mixture of 1,4-benzene diboronic acid (1.00 g, 6.0 mmol), butyl 4-iodobenzoate (4.04 g, 13 mmol), sodium carbonate (1.92 g, 18 mmol), 1,2-dimethoxyethane (25 mL), ethanol (7 mL), and water (10 mL) was deaerated by sparing with nitrogen for 10 min. Dichlorobis(triphenylphosphine)-palladium(II) (0.085 g, 0.12 mmol) was added, and the sparging was continued for 5 min. The stirred reaction mixture was held at reflux under nitrogen for 44 h and then cooled to ambient. Dichloromethane (100 mL) and water (100 mL) were added. The organic layer was separated dried (MgSO4), passed through a short column of silica gel to remove residual catalyst, and concentrated to deposit a crude product. The product was purified by column chromatography followed by recrystallization from heptane and then from acetonitrile. The product was obtained as white needles, mass: 1.45 g (56% of theory). 1H NMR (CDCl3): δ 1.00 (t, 6H), 1.5 (m, 4H), 1.8 (m, 4H), 4.36 (q, 4H), 7.75 (m, 8H), 8.13 (d, 4H).

Workup

  1. waitthe sparging was continued for 5 min
  2. customThe stirred reaction mixture
  3. temperatureat reflux under nitrogen for 44 h
  4. temperaturecooled
  5. customThe organic layer was separated
  6. dry with materialdried (MgSO4)
  7. customto remove residual catalyst
  8. concentrationconcentrated
  9. customThe product was purified by column chromatography
  10. customfollowed by recrystallization from heptane
  11. customThe product was obtained as white needles, mass

Sources & evidence

ORD record
ord-166ec6b202a04ac38571096c726a11b7
Source dataset
uspto-grants-2008_12
Patent number
US07459263B2

Reaction notes

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