Hydrochloric Acid → HCID 59147628, compound

HRID 1640354Notes

Reaction equation

HRID 1640354 reaction equation
C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.Br[C:24]1[CH:25]=[C:26]2[C:31](=[CH:32][CH:33]=1)[CH:30]=[C:29]([OH:34])[CH:28]=[CH:27]2.[C:35]1(B(O)O)[C:44]2[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=2)[CH:38]=[CH:37][CH:36]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].Cl>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.O1CCOCC1>[C:43]1([C:24]2[CH:25]=[C:26]3[C:31](=[CH:32][CH:33]=2)[CH:30]=[C:29]([OH:34])[CH:28]=[CH:27]3)[C:44]2[C:39](=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH:40]=[CH:41][CH:42]=1

Participants

10

Reactant 5

HCID 313Hydrochloric AcidHCID 271446-Bromo-2-naphthalenolHCID 62657Potassium Phosphate, TribasicHCID 80271Tri-o-tolylphosphineHCID 2545321-Naphthaleneboronic acid

Product 1

HCID 59147628HCID 59147628, compound

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 312751,4-DioxaneSolvent

Procedure

913 mg (3 mmol) of tri-o-tolylphosphine and then 112 mg (0.5 mmol) of palladium(II) acetate are added to a suspension of 111.5 g (500 mmol) of 6-bromo-2-naphthol, 111.8 g (650 mmol) of naphthaleneboronic acid and 224.1 g (1150 mmol) of tripotassium phosphate in a mixture of 1000 ml of toluene, 200 ml of dioxane and 1000 ml of water, and the mixture is heated under reflux for 18 h. After cooling, 200 ml of 2 N hydrochloric acid are added, and the organic phase is separated off, washed three times with 500 ml of 1 N hydrochloric acid, once with 500 ml of saturated sodium chloride solution, filtered through silica gel and evaporated to dryness in vacuo. The residue is recrystallised from 150 ml of toluene. Yield: 113.3 g (419 mmol), 83.8% of theory; purity: 98% according to NMR.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 18 h
  3. temperatureAfter cooling
  4. customthe organic phase is separated off
  5. washwashed three times with 500 ml of 1 N hydrochloric acid
  6. filtrationonce with 500 ml of saturated sodium chloride solution, filtered through silica gel
  7. customevaporated to dryness in vacuo
  8. customThe residue is recrystallised from 150 ml of toluene

Sources & evidence

ORD record
ord-5e4d00f6941f40e988a79b29004c49f1
Source dataset
uspto-grants-2012_02
Patent number
US08114531B2

Reaction notes

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