Dichloromethane → HCID 59147628, compound

HRID 519418Notes

Reaction equation

HRID 519418 reaction equation
[C:1]1(B(O)O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.FC(F)(F)S([O:19][C:20]1[CH:29]=[CH:28][C:27]2[C:22](=[CH:23][CH:24]=[C:25](O)[CH:26]=2)[CH:21]=1)(=O)=O.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C(Cl)Cl>C1COCC1.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].C1(C2C=CC=CC=2)C=CC=CC=1P(C1CCCCC1)C1CCCCC1>[C:1]1([C:25]2[CH:24]=[CH:23][C:22]3[C:27](=[CH:28][CH:29]=[C:20]([OH:19])[CH:21]=3)[CH:26]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 62657Potassium Phosphate, TribasicHCID 2545321-Naphthaleneboronic acidHCID 10935209HCID 10935209, compound

Product 1

HCID 59147628HCID 59147628, compoundYield 120.9%

Reagents, catalysts & solvents 3

HCID 27342162-(Dicyclohexylphosphino)biphenylCatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Naphthalen-1-ylboronic acid (5.30 g, 30.8 mmol), 6-hydroxynaphthalen-2-yl trifluoromethanesulfonate (7.5 g, 25.7 mmol), potassium phosphate (10.90 g, 51.3 mmol) were mixed in 200 mL of THF and 20 mL of water and bubbled with nitrogen for 20 minutes. Pd2(dba)3 (0.235 g, 0.257 mmol) and [1,1′-biphenyl]-2-yldicyclohexylphosphine (0.180 g, 0.513 mmol) were added to the reaction mixture. The reaction was refluxed overnight. After cooling, the reaction mixture was extracted with ethyl acetate and washed with brine. The organic layer was separated and dried over MgSO4. The residue was purified by column using 1:2 hexanes:DCM (v/v) to give [1,2′-binaphthalen]-6′-ol (8.4 g, 95% yield).

Workup

  1. custom20 mL of water and bubbled with nitrogen for 20 minutes
  2. temperatureThe reaction was refluxed overnight
  3. temperatureAfter cooling
  4. extractionthe reaction mixture was extracted with ethyl acetate
  5. washwashed with brine
  6. customThe organic layer was separated
  7. dry with materialdried over MgSO4
  8. customThe residue was purified by column

Sources & evidence

ORD record
ord-ed2c7dd7836d429d8ee043fc2a9d7518
Source dataset
uspto-grants-2015_08
Patent number
US09118017B2

Reaction notes

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