Diethyl Ether → HCID 86707585, compound

HRID 2279975Notes

Reaction equation

HRID 2279975 reaction equation
[OH-].[NH3+]N.Br[C:5]1[CH:6]=[C:7]([OH:12])[CH:8]=[C:9](Br)[CH:10]=1.[CH2:13]([O:20][C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[CH3:30][CH2:31][O:32][CH2:33][CH3:34]>O.C1COCC1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[CH2:13]([O:20][C:21]1[CH:26]=[CH:25][C:24]([C:5]2[CH:6]=[C:7]([OH:12])[CH:8]=[C:9]([C:21]3[CH:22]=[CH:23][C:31]([O:32][CH2:33][C:34]4[CH:18]=[CH:19][CH:14]=[CH:15][CH:16]=4)=[CH:30][CH:26]=3)[CH:10]=2)=[CH:23][CH:22]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

8

Reactant 4

HCID 3283Diethyl EtherHCID 122803,5-DibromophenolHCID 27343144-Benzyloxy-phenylboronic acidHCID 44558531Aminoammonium hydroxide

Product 1

HCID 86707585HCID 86707585, compound

Reagents, catalysts & solvents 3

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

8.85 (64 mmol) sodium metaborate-tetrahydrate are dissolved in 100 ml water, 570 mg (0.794 mmol) bis(triphenylphosphine)palladium(II)chloride, 0.2 ml hydraziniumhydroxide and 10.0 g (39.7 mmol) 3,5-dibromophenol in 100 ml THF are added, and after 5 min a solution of 24.0 g (105 mmol) 4-benzyloxybenzeneboronic acid in 200 ml THF are added. The mixture is heated overnight at reflux, MTB ether is added, the aqueous layer is separated and extracted three times with MTB ether. The combined organic layers are washed with sat. aq. sodium chloride solution and dried over sodium sulfate. The solvent is removed in vacuo and the residue is filtered through silica gel with heptane/toluene (8:2) and recrystallized from ethanol, to give 4,4″-bis-benzyloxy-[1,1′;3′,1″]terphenyl-5′-ol as colourless crystals.

Workup

  1. temperatureThe mixture is heated overnight
  2. temperatureat reflux
  3. customthe aqueous layer is separated
  4. extractionextracted three times with MTB ether
  5. washThe combined organic layers are washed with sat. aq. sodium chloride solution
  6. dry with materialdried over sodium sulfate
  7. customThe solvent is removed in vacuo
  8. filtrationthe residue is filtered through silica gel with heptane/toluene (8:2)
  9. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-95e9fc50631d417189f29a02d39f5b56
Source dataset
uspto-grants-2015_09
Patent number
US09133395B2

Reaction notes

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