Potassium Carbonate → HCID 59728411, compound

HRID 1797824Notes

Reaction equation

HRID 1797824 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](Br)=[CH:17][C:16]=1[N+:22]([O-:24])=[O:23].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+:22]([C:16]1[CH:17]=[C:18]([C:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:4]=[CH:3][CH:2]=2)[CH:19]=[CH:20][C:15]=1[C:9]1[C:10]2[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=2)[CH:6]=[CH:7][CH:8]=1)([O-:24])=[O:23]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 770041,4-Dibromo-2-nitrobenzeneHCID 2545321-Naphthaleneboronic acid

Product 1

HCID 59728411HCID 59728411, 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 67.8 g (190 mmol) of 1-naphthylboronic acid, 53.3 g (190 mmol) of 2,5-dibromonitrobenzene and 137.9 g (648.5 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 subsequently dried in vacuo; yield: 86.1 g, 71% of theory; purity: 98.4% 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. customsubsequently dried in vacuo

Sources & evidence

ORD record
ord-ad49d8b7614340af93a57211f65ca52d
Source dataset
uspto-grants-2013_01
Patent number
US08343637B2

Reaction notes

Loading…