Potassium Carbonate → HCID 59500462, compound

HRID 452051Notes

Reaction equation

HRID 452051 reaction equation
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:11]1[CH:16]=[CH:15][C:14](Br)=[CH:13][C:12]=1[N+:18]([O-:20])=[O:19].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>[N+:18]([C:2]1[CH:3]=[C:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:5]=[CH:6][C:1]=1[C:11]1[CH:16]=[CH:15][C:14]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:1]=2)=[CH:13][C:12]=1[N+:18]([O-:20])=[O:19])([O-:20])=[O:19]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 770041,4-Dibromo-2-nitrobenzene

Product 1

HCID 59500462HCID 59500462, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

2.4 g (2.1 mmol) of Pd(PPh3)4 are added to a well-stirred, degassed suspension of 18.8 g (154.5 mmol) of phenylboronic acid, 30 g (74.6 mmol) of 2,5-dibromonitrobenzene and 53 g (212.7 mmol) of potassium carbonate in a mixture of 300 ml of water and 300 ml of THF, and the mixture is heated under reflux for 20 hours. 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, 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: 23 g, 80% of theory; purity: 99.2% according to HPLC.

Workup

  1. customdegassed
  2. temperaturethe mixture is heated
  3. temperatureunder reflux for 20 hours
  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 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-470faa63989d4338ac7a1b763c006601
Source dataset
uspto-grants-2013_07
Patent number
US08487300B2

Reaction notes

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