Sodium Carbonate → HCID 67775727, compound

HRID 2206825Notes

Reaction equation

HRID 2206825 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11](B(O)O)=[C:10]([O:17][CH3:18])[C:9]=1[O:19][CH3:20].[F:21][C:22]1[CH:27]=[CH:26][C:25]([Br:28])=[CH:24][C:23]=1I.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1>[Br:28][C:25]1[CH:24]=[CH:23][C:22]([F:21])=[C:27]([C:11]2[CH:12]=[CH:13][C:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[F:1])=[C:9]([O:19][CH3:20])[C:10]=2[O:17][CH3:18])[CH:26]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 27827504-Bromo-1-fluoro-2-iodobenzeneHCID 677757472'-Fluoro-2,3-dimethoxybiphenyl-4-boronic acid

Product 1

HCID 67775727HCID 67775727, compoundYield 80.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In the atmosphere of argon, 15.2 g of 2′-fluoro-2,3-dimethoxybiphenyl-4-boronic acid, 16.5 g of 2-fluoro-5-bromoiodobenzene, 1.27 g of tetrakistriphenylphosphine palladium (0), 180 mL of toluene and 90 mL of an aqueous 2M sodium carbonate solution were placed in a flask. The resulting solution was stirred with heating under reflux for 8 hours. After cooling to room temperature, the reaction solution was extracted with toluene. An aqueous phase was removed, and an organic phase was washed with saturated saline. The organic phase was dried with magnesium sulfate, and concentrated. Residues were purified by means of silica gel column chromatography, whereby 17.8 g (yield: 80%) of 5-bromo-2-fluoro-2′,3′-dimethoxy-2″-fluoro-p-terphenyl was obtained.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 8 hours
  3. extractionthe reaction solution was extracted with toluene
  4. customAn aqueous phase was removed
  5. washan organic phase was washed with saturated saline
  6. dry with materialThe organic phase was dried with magnesium sulfate
  7. concentrationconcentrated
  8. customResidues were purified by means of silica gel column chromatography

Sources & evidence

ORD record
ord-3bb4f4dc6251448da7171da6aeeeb3a2
Source dataset
uspto-grants-2016_06
Patent number
US09373792B2

Reaction notes

Loading…