Chloride → HCID 10670667, compound

HRID 1622048Notes

Reaction equation

HRID 1622048 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([OH:24])[C:8]=2[C:12]2[C:13]([OH:23])=[CH:14][CH:15]=[C:16]3[C:21]=2[CH:20]=[CH:19][C:18](Br)=[CH:17]3)[CH:3]=1.[Cl-].O.NN.[C:29]1(B(O)O)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>O.C1COCC1>[C:29]1([C:18]2[CH:19]=[CH:20][C:21]3[C:16](=[CH:15][CH:14]=[C:13]([OH:23])[C:12]=3[C:8]3[C:7]([OH:24])=[CH:6][CH:5]=[C:4]4[C:9]=3[CH:10]=[CH:11][C:2]([C:2]3[CH:11]=[CH:10][CH:9]=[CH:4][CH:3]=3)=[CH:3]4)[CH:17]=2)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

7

Reactant 4

HCID 312ChlorideHCID 24654Hydrazine hydrate (1:1)HCID 66827Phenylboronic AcidHCID 2228426,6′-Dibromo[1,1′-binaphthalene]-2,2′-diol

Product 1

HCID 10670667HCID 10670667, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

12.0 g (25.7 mmol) of (±)-6,6′-dibromo[1,1′]binaphthalinyl-2,2′-diol, 11.5 g (41 mmol) of sodium metaborate octahydrate and 800 mg of bistriphenylphosphinepalladium(II) chloride are initially introduced in 100 ml of water and 20 ml of THF, 0.13 ml of hydrazine hydrate is added, and a solution of 7.0 g (57 mmol) of benzeneboronic acid in 80 ml of THF is added dropwise. The batch is subsequently heated under reflux overnight, added to water and extracted three times with MTB ether. The combined org. phases are washed with water and dried over sodium sulfate. The solvent is removed in vacuo, and the residue is filtered through silica gel with toluene/ethyl acetate (19:1) and evaporated, and the product is recrystallized once each from toluene/cyclohexane (1:1) and isopropanol, giving (±)-6,6′-diphenyl[1,1′]binaphthalinyl-2,2′-diol as colorless crystals.

Workup

  1. temperatureThe batch is subsequently heated
  2. temperatureunder reflux overnight
  3. extractionextracted three times with MTB ether
  4. washphases are washed with water
  5. dry with materialdried over sodium sulfate
  6. customThe solvent is removed in vacuo
  7. filtrationthe residue is filtered through silica gel with toluene/ethyl acetate (19:1)
  8. customevaporated
  9. customthe product is recrystallized once each from toluene/cyclohexane (1:1) and isopropanol

Sources & evidence

ORD record
ord-1c127da9e2dd4a9db4c55d77480e95d7
Source dataset
uspto-grants-2014_07
Patent number
US08778466B2

Reaction notes

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