Ethanol → HCID 21889342, compound

HRID 720230Notes

Reaction equation

HRID 720230 reaction equation
Br[C:2]1[C:7]2[CH:8]=[CH:9][CH:10]=[C:11]3[C:12](=[O:26])[C:13]4[CH:24]=[C:23](Br)[C:16]5=[CH:17][CH:18]=[CH:19][C:20]6[C:21](=[O:22])[C:4](=[C:5]([C:14]=4[C:15]=65)[C:6]=23)[CH:3]=1.[C:27]1(B(O)O)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C(O)C.C(=O)([O-])[O-].[K+].[K+].[C:45]1(C)[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1>>[C:27]1([C:2]2[C:7]3[CH:8]=[CH:9][CH:10]=[C:11]4[C:12](=[O:26])[C:13]5[CH:24]=[C:23]([C:45]6[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=6)[C:16]6=[CH:17][CH:18]=[CH:19][C:20]7[C:21](=[O:22])[C:4](=[C:5]([C:14]=5[C:15]=76)[C:6]=34)[CH:3]=2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

6

Reactant 5

HCID 702EthanolHCID 1140TolueneHCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 78084C.I. Vat Orange 3

Product 1

HCID 21889342HCID 21889342, compound

Procedure

To a 3 L of three neck flask were charged with 30 0 g (0.065 mol.) of 4,10-Dibromo-dibenzo[def,mno]chrysene-6,12-dione, 17.8 g (0.146 mol.) of phenyl boronic acid, and 0.2 g of 18-c-6 in a mixture of 1200 mL of toluene, 300 mL of ethanol, and 250 mL of 2.0 N potassium carbonate. After mixture was bubbled with house nitrogen for 15 min, 0.3 g of Pd (PPh3)4 was added to the reaction mixture under nitrogen. Then the reaction mixture was heated to reflux with efficient stirring under nitrogen protection. After the reaction proceeded for three hours, 0.2 g of Pd (PPh3)4 was added to the reaction mixture under nitrogen. The reaction mixture was continued to reflux for overnight. The newly formed orange solid was suspended in organic layer. After cool the reaction mixture to room temperature, the water phase was separated. The organic layer (with newly formed orange solid was suspended) was washed with water for three times (3×300 mL). The orange precipitates was filtered and washed with acetone (for easy dry). A 28.8 g of pure 4,10-Diphenyl-dibenzo[def,mno]chrysene-6,12-dione was obtained. Yield is in 96.5%.

Workup

  1. customAfter mixture was bubbled with house nitrogen for 15 min
  2. addition0.3 g of Pd (PPh3)4 was added to the reaction mixture under nitrogen
  3. temperatureThen the reaction mixture was heated
  4. temperatureto reflux
  5. addition0.2 g of Pd (PPh3)4 was added to the reaction mixture under nitrogen
  6. temperatureto reflux for overnight
  7. customthe water phase was separated
  8. washwas washed with water for three times (3×300 mL)
  9. customThe orange precipitates
  10. filtrationwas filtered
  11. washwashed with acetone (for easy dry)

Sources & evidence

ORD record
ord-4d441fd0c3c641efb3834dd60cf327a1
Source dataset
uspto-grants-2006_11
Patent number
US07135243B2

Reaction notes

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