1,2,4-Trimethylbenzene → HCID 86701346, compound

HRID 2179847Notes

Reaction equation

HRID 2179847 reaction equation
[C:1]1([C:11]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:18](B(O)O)=[C:17]3[C:12]=2[CH:13]=[CH:14][CH:15]=[CH:16]3)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.FC(F)(F)S(O[C:34]1[CH:43]=[CH:42][C:41]2[C:36](=[CH:37][C:38]([O:44][CH3:45])=[CH:39][CH:40]=2)[CH:35]=1)(=O)=O.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(C(=CC(=CC=1)C)C)C>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.CC(O)C>[CH3:45][O:44][C:38]1[CH:37]=[C:36]2[C:41]([CH:42]=[CH:43][C:34]([C:18]3[C:17]4[C:12]([C:11]([C:1]5[C:10]6[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=6)[CH:4]=[CH:3][CH:2]=5)=[C:24]5[C:19]=3[CH:20]=[CH:21][CH:22]=[CH:23]5)=[CH:13][CH:14]=[CH:15][CH:16]=4)=[CH:35]2)=[CH:40][CH:39]=1

Participants

8

Reactant 4

HCID 72471,2,4-TrimethylbenzeneHCID 62657Potassium Phosphate, TribasicHCID 10892112Methanesulfonic acid, trifluoro-, 7-methoxy-2-naphthalenyl esterHCID 23088558[10-(Naphthalen-1-yl)anthracen-9-yl]boronic acid

Product 1

HCID 86701346HCID 86701346, compoundYield 52.7%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×HCID 3776IsopropanolSolvent

Procedure

Under the nitrogen atmosphere, (10-(naphthalen-1-yl)anthracen-9-yl)boronic acid (25.1 g), 7-methoxynaphthalen-2-yl trifluoromethane sulfonate (24.3 g), Pd(PPh3)4 (0.9 g), potassium phosphate (30.6 g), and a mixture solvent (260 ml) of pseudo cumene, IPA, and water (pseudo cumene/IPA/water=8/4/1 (volume ratio)) were added to a flask and refluxed for 4.5 hours. Once the heating is completed, water was added. After cooling to room temperature, a solid was collected by suction filtration. The obtained solid was washed with water and subsequently with methanol, dissolved in toluene, and purified with a silica gel short column. Crystals obtained by slow distillation of the solvent under reduced pressure were collected by suction filtration to give 9-(7-methoxynaphthalen-2-yl)-10-(naphthalen-1-yl)anthracene (17.5 g) as a third intermediate compound. The scheme is shown in the following “Reaction 4”.

Workup

  1. temperaturerefluxed for 4.5 hours
  2. filtrationa solid was collected by suction filtration
  3. washThe obtained solid was washed with water and subsequently with methanol
  4. dissolutiondissolved in toluene
  5. custompurified with a silica gel short column
  6. customCrystals obtained by slow distillation of the solvent under reduced pressure
  7. filtrationwere collected by suction filtration

Sources & evidence

ORD record
ord-046678364a4646ae9a449b0b6bb6b3d4
Source dataset
uspto-grants-2015_06
Patent number
US09070885B2

Reaction notes

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