Sodium Carbonate → HCID 24865705, compound

HRID 1015955Notes

Reaction equation

HRID 1015955 reaction equation
[Br:1][C:2]1[CH:7]=[C:6](I)[C:5](I)=[CH:4][C:3]=1[Br:10].[C:11]1(B(O)O)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(=O)([O-])[O-].[Na+].[Na+]>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.O.C1(C)C=CC=CC=1.C(O)C>[Br:1][C:2]1[CH:7]=[C:6]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:5]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:4][C:3]=1[Br:10]

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 114203921,2-dibromo-4,5-diiodobenzene

Product 1

HCID 24865705HCID 24865705, compoundYield 159.8%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolvent2×HCID 1140TolueneSolvent2×

Conditions

Temperature
82 °C

Procedure

To a 200 ml Schlenk reaction vessel were added under a nitrogen atmosphere 3.074 g (6.30 mmol) of 1,2-dibromo-4,5-diiodobenzene synthesized in Synthetic Example 3, 600 mg (0.519 mmol) of tetrakis(triphenylphosphine)palladium (manufactured by Tokyo Chemical Industry Co. Ltd.), and 1.920 mg (15.7 mmol) of phenylboronic acid (manufactured by Wako Pure Chemical Industries, Ltd.). Further, 50 ml of toluene, 13 ml of ethanol, and an aqueous solution composed of 4.007 g (37.8 mol) of sodium carbonate and 16 ml of water were added. The whole was heated to 82° C. and stirred for 24 hours. After cooling to room temperature, toluene and water were added and phase separation was conducted. The organic phase was concentrated and the resulting residue was dissolved in 26 ml of toluene. Then, 1.0 ml of a 70% tert-butyl hydroperoxide solution (manufactured by Wako Pure Chemical Industries, Ltd.) was added thereto, followed by 2 hours of stirring at room temperature. The toluene solution was washed twice with water and then the organic phase was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent: hexane) to obtain a white solid of 1,2-dibromo-4,5-diphenylbenzene (1.953 g, yield 80%).

Workup

  1. additionwere added
  2. temperatureAfter cooling to room temperature
  3. customphase separation
  4. concentrationThe organic phase was concentrated
  5. dissolutionthe resulting residue was dissolved in 26 ml of toluene
  6. additionThen, 1.0 ml of a 70% tert-butyl hydroperoxide solution (manufactured by Wako Pure Chemical Industries, Ltd.) was added
  7. waitfollowed by 2 hours
  8. stirringof stirring at room temperature
  9. washThe toluene solution was washed twice with water
  10. concentrationthe organic phase was concentrated under reduced pressure
  11. customThe obtained residue was purified by silica gel column chromatography (solvent: hexane)

Sources & evidence

ORD record
ord-0c4b0689b45c4a04b7482e301d9b2bd8
Source dataset
uspto-grants-2011_07
Patent number
US07985885B2

Reaction notes

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