Phosphate → HCID 59776006, compound

HRID 403137Notes

Reaction equation

HRID 403137 reaction equation
Br[C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[C:12]1(B(O)O)[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15](B(O)O)=[CH:14][CH:13]=1.P([O-])([O-])([O-])=O>O.C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:7][O:6][C:4]([C:3]1[CH:8]=[CH:9][CH:10]=[CH:11][C:2]=1[C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]([C:2]2[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=2[C:4]([O:6][CH3:7])=[O:5])=[CH:14][CH:13]=1)=[O:5]

Participants

7

Reactant 3

HCID 1061PhosphateHCID 11894Methyl 2-bromobenzoateHCID 10488882NAPHTHALENE-1,4-DIBORONIC ACID

Product 1

HCID 59776006HCID 59776006, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

1.55 g (0.1 mmol) of Pd(PPh3)4 are added to a vigorously stirred, degassed suspension of 21.6 g (7.1 mmol) of methyl 2-bromobenzoate, 10.1 g (28 mmol) of 1,4-naphthalenediboronic acid and 18.9 g (6.6 mmol) of trispotassium phosphate in a mixture of 350 ml of water and 350 ml of THF, and the mixture is refluxed for 60 h. After cooling, the organic phase is separated off, washed three times with 200 ml of water and once with 200 ml of saturated sodium chloride solution and subsequently dried over magnesium sulfate. The organic phase is evaporated to dryness under reduced pressure in a rotary evaporator. The grey residue obtained in this way is recrystallised from dioxane. The deposited crystals are filtered off with suction, washed with 50 ml of ethanol and subsequently dried under reduced pressure. Yield: 13 g, 82% of theory.

Workup

  1. customdegassed
  2. temperaturethe mixture is refluxed for 60 h
  3. temperatureAfter cooling
  4. customthe organic phase is separated off
  5. washwashed three times with 200 ml of water
  6. dry with materialonce with 200 ml of saturated sodium chloride solution and subsequently dried over magnesium sulfate
  7. customThe organic phase is evaporated to dryness under reduced pressure in a rotary evaporator
  8. customThe grey residue obtained in this way
  9. customis recrystallised from dioxane
  10. filtrationThe deposited crystals are filtered off with suction
  11. washwashed with 50 ml of ethanol
  12. customsubsequently dried under reduced pressure

Sources & evidence

ORD record
ord-d6fc4921cd544226ac7b590a57202f6b
Source dataset
uspto-grants-2014_06
Patent number
US08748010B2

Reaction notes

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