Sodium Carbonate → HCID 23067328, compound

HRID 1712230Notes

Reaction equation

HRID 1712230 reaction equation
[C:1]1([C:7]2[CH:12]=[CH:11][C:10]([C:13]3[CH:14]=[C:15]([C:19]4[C:20]5[C:25]([C:26](Br)=[C:27]6[C:32]=4[CH:31]=[CH:30][CH:29]=[CH:28]6)=[CH:24][CH:23]=[CH:22][CH:21]=5)[CH:16]=[CH:17][CH:18]=3)=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:34]1([C:40]([C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)=[CH:41][C:42]2[CH:47]=[CH:46][C:45](OB(O)O)=[CH:44][CH:43]=2)[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.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>[C:1]1([C:7]2[CH:12]=[CH:11][C:10]([C:13]3[CH:14]=[C:15]([C:19]4[C:20]5[C:25]([C:26]([C:45]6[CH:46]=[CH:47][C:42]([CH:41]=[C:40]([C:52]7[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=7)[C:34]7[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=7)=[CH:43][CH:44]=6)=[C:27]6[C:32]=4[CH:31]=[CH:30][CH:29]=[CH:28]6)=[CH:24][CH:23]=[CH:22][CH:21]=5)[CH:16]=[CH:17][CH:18]=3)=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 23020580HCID 23020580, compoundHCID 23067337HCID 23067337, compound

Product 1

HCID 23067328HCID 23067328, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent2×

Procedure

Under an atmosphere of argon, 9-(3-(4-phenylphenyl)phenyl)-10-bromoanthracene (3.0 g, 6.2 mmole), 4-(2,2-diphenylvinyl)phenylboric acid (2.0 g, 6.7 mmole, 1.1 eq) and tetrakis(triphenylphosphine)palladium(0) (0.14 g, 0.12 mmole, 2% Pd) were suspended in toluene (20 ml). To the obtained suspension, a 2M aqueous solution of sodium carbonate (2.1 g, 20 mmole, 3 eq/10 ml) was added, and the resultant mixture was refluxed for 10 hours. The reaction mixture was filtered and washed with water and methanol, and a light yellow solid substance was obtained. The obtained solid substance was suspended in boiling toluene (30 ml). After the suspension was cooled while being left standing, the suspension was filtered, and a light yellow solid substance (3.0 g, the yield: 73%) was obtained. The result of examination of the obtained product in accordance with 1H-NMR was as follows:

Workup

  1. filtrationThe reaction mixture was filtered
  2. washwashed with water and methanol
  3. customa light yellow solid substance was obtained
  4. temperatureAfter the suspension was cooled
  5. waitwhile being left standing
  6. filtrationthe suspension was filtered
  7. customa light yellow solid substance (3.0 g, the yield: 73%) was obtained
  8. customThe result of examination of the obtained product in accordance with 1H-NMR

Sources & evidence

ORD record
ord-597bae4a737e471892677a30b0b85a8d
Source dataset
uspto-grants-2010_09
Patent number
US07790892B2

Reaction notes

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