Potassium Carbonate → HCID 57997803, compound

HRID 1797822Notes

Reaction equation

HRID 1797822 reaction equation
[C:1]1([CH3:10])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1B(O)O.Br[C:12]1[CH:17]=[CH:16][C:15](Br)=[CH:14][C:13]=1[N+:19]([O-:21])=[O:20].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>[CH3:10][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:12]1[CH:17]=[CH:16][C:15]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=2[CH3:10])=[CH:14][C:13]=1[N+:19]([O-:21])=[O:20]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 770041,4-Dibromo-2-nitrobenzeneHCID 27332672-Methylphenyl boronic acid

Product 1

HCID 57997803HCID 57997803, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

5.46 g (4.7 mmol) of Pd(PPh3)4 are added to a well-stirred, degassed suspension of 155 g (1140 mmol) of o-tolylboronic acid, 133.4 g (474.9 mmol) of 2,5-dibromonitrobenzene and 305.3 g (1435 mmol) of potassium carbonate in a mixture of 250 ml of water and 250 ml of THF, and the mixture is heated under reflux for 20 h. After cooling, the organic phase is separated off, washed three times with 200 ml of water and once with 200 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: 50.5 g, 97% of theory; purity: 99.2% according to HPLC.

Workup

  1. customdegassed
  2. temperaturethe mixture is heated
  3. temperatureunder reflux for 20 h
  4. temperatureAfter cooling
  5. customthe organic phase is separated off
  6. washwashed three times with 200 ml of water
  7. dry with materialonce with 200 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-a831ae7b96ce4238b51efb4287bf2b5d
Source dataset
uspto-grants-2013_01
Patent number
US08343637B2

Reaction notes

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