Sodium Carbonate → HCID 67776685, compound

HRID 2206832Notes

Reaction equation

HRID 2206832 reaction equation
[CH:1]1[C:13]2[C:12]3[O:11][C:10]4[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=4[C:8]=3[CH:7]=[C:6](B(O)O)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[Br:21][C:22]1[CH:23]=[C:24](I)[CH:25]=[CH:26][CH:27]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1>[Br:21][C:22]1[CH:23]=[C:24]([C:6]2[C:5]3[CH:4]=[CH:3][CH:2]=[CH:1][C:13]=3[C:12]3[O:11][C:10]4[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=4[C:8]=3[CH:7]=2)[CH:25]=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 11561Benzene, 1-bromo-3-iodo-HCID 67777161HCID 67777161, compound

Product 1

HCID 67776685HCID 67776685, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In the atmosphere of argon, 17.0 g of benzo[b]naphtho[2,1-d]furan-5-boronic acid, 18.4 g of 3-bromoiodobenzene, 1.50 g of tetrakistriphenylphosphine palladium (0), 200 mL of toluene and 100 mL of a 2M aqueous sodium carbonate solution were placed in a flask. The resulting mixture 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. An organic phase was dried with magnesium sulfate and concentrated. Residues were purified by silica gel column chromatography, whereby 21.8 g of 5-(3-bromophenyl)benzo[b]naphtho[2,1-d]furan 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. dry with materialAn organic phase was dried with magnesium sulfate
  6. concentrationconcentrated
  7. customResidues were purified by silica gel column chromatography

Sources & evidence

ORD record
ord-894142f86a534f4aa423eb9b3877f258
Source dataset
uspto-grants-2016_06
Patent number
US09373792B2

Reaction notes

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