Potassium Carbonate → HCID 57997746, compound

HRID 1797823Notes

Reaction equation

HRID 1797823 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.Br[C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[C:17]([N+:27]([O-:29])=[O:28])[CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>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>[C:1]1([C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[C:17]([N+:27]([O-:29])=[O:28])[CH:16]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 2545321-Naphthaleneboronic acidHCID 15688873HCID 15688873, compound

Product 1

HCID 57997746HCID 57997746, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

1.62 g (1.40 mmol) of Pd(PPh3)4 are added to a well-stirred, degassed suspension of 46 g (268 mmol) of 1-naphthylboronic acid, 71 g (255.3 mmol) of 4-bromo-2-nitrobiphenyl and 93 g (433.9 mmol) of potassium carbonate in a mixture of 700 ml of water and 700 ml of THF, and the mixture is heated under reflux for 17 h. After cooling, the organic phase is separated off, washed three times with 400 ml of water and once with 400 ml of saturated, aqueous sodium chloride solution, dried over magnesium sulfate and evaporated to dryness in vacuo in a rotary evaporator. The grey residue is recrystallised from hexane. The deposited crystals are filtered off with suction, washed with a little MeOH and dried in vacuo; yield: 83.1 g, 97.9% of theory; purity: 99.0% according to HPLC.

Workup

  1. customdegassed
  2. temperaturethe mixture is heated
  3. temperatureunder reflux for 17 h
  4. temperatureAfter cooling
  5. customthe organic phase is separated off
  6. washwashed three times with 400 ml of water
  7. dry with materialonce with 400 ml of saturated, aqueous sodium chloride solution, dried over magnesium sulfate
  8. customevaporated to dryness in vacuo in a rotary evaporator
  9. customThe grey residue is recrystallised from hexane
  10. filtrationThe deposited crystals are filtered off with suction
  11. washwashed with a little MeOH
  12. customdried in vacuo

Sources & evidence

ORD record
ord-84c0c9f53970448bb37461c0066df359
Source dataset
uspto-grants-2013_01
Patent number
US08343637B2

Reaction notes

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