Hydrochloric Acid → HCID 86623428, compound

HRID 1629662Notes

Reaction equation

HRID 1629662 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2(O)[C:25]3[C:16](=[CH:17][C:18]4[C:23]([CH:24]=3)=[CH:22][CH:21]=[CH:20][CH:19]=4)[C:15]([C:27]3[CH:32]=[CH:31][C:30]([Br:33])=[CH:29][CH:28]=3)(O)[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]2=3)=[CH:4][CH:3]=1.Cl.C1(C)C=CC=CC=1>C(O)(=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:25]3[C:16](=[CH:17][C:18]4[C:23]([CH:24]=3)=[CH:22][CH:21]=[CH:20][CH:19]=4)[C:15]([C:27]3[CH:28]=[CH:29][C:30]([Br:33])=[CH:31][CH:32]=3)=[C:14]3[C:9]=2[CH:10]=[CH:11][CH:12]=[CH:13]3)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric Acid3×HCID 1140TolueneHCID 69246674HCID 69246674, compound

Product 1

HCID 86623428HCID 86623428, compoundYield 81.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent3×

Procedure

Into a 300-cm3 eggplant-shaped flask filled with air, 3.0 g (5.22×10−3 mol) of 5,12-bis(4-bromophenyl)-5,12-dihydroxytetracene synthesized as described above was weighed. Into the eggplant-shaped flask, 150 cm3 of acetic acid, which was used as a solvent, was poured, whereby an acetic acid solution was prepared. Stannous chloride and a 35% of aqueous solution of hydrochloric acid were mixed at a weight ratio of 1:1, whereby a hydrochloric acid solution of stannous chloride was prepared. To the acetic acid solution, 20 cm3 of the hydrochloric acid solution was added. The solution mixture was subjected to reaction for three hours at room temperature. The reaction mixture was transferred to a separatory funnel. Toluene was added to the reaction mixture. This mixture was sufficiently washed with distilled water. The organic layer in the separatory funnel was dried with 5 g of magnesium sulfate. The solvents were removed from the organic layer in an evaporator, whereby a white solid was obtained. The white solid was purified by silica gel chromatography using a mixture containing toluene and hexane at a ratio of 1:2 and reprecipitation using dichloromethane and hexane, whereby 2.3 g of 5,12-bis(4-bromophenyl)-tetracene was obtained as shown in FIG. 6. The yield of 5,12-bis(4-bromophenyl)-tetracene was 82%.

Workup

  1. customsynthesized
  2. additionwas poured
  3. customwas prepared
  4. customThe solution mixture was subjected to reaction for three hours at room temperature
  5. customThe reaction mixture was transferred to a separatory funnel
  6. washThis mixture was sufficiently washed with distilled water
  7. dry with materialThe organic layer in the separatory funnel was dried with 5 g of magnesium sulfate
  8. customThe solvents were removed from the organic layer in an evaporator, whereby a white solid
  9. customwas obtained
  10. customThe white solid was purified by silica gel chromatography
  11. additioncontaining toluene and hexane
  12. customat a ratio of 1:2 and reprecipitation

Sources & evidence

ORD record
ord-2cffc32c9f7d4cd48a9a9cf7fdb5380f
Source dataset
uspto-grants-2014_07
Patent number
US08790792B2

Reaction notes

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