Water → HCID 86606381, compound

HRID 1882350Notes

Reaction equation

HRID 1882350 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]1[C:24]2[C:25]3=[C:26]4[C:21](=[CH:22][CH:23]=2)[CH:20]=[CH:19][C:18]([C:27]2[CH:36]=[CH:35][C:34]5[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=5)[CH:28]=2)=[C:17]4[CH:16]=[CH:15][C:14]3=[CH:13][CH:12]=1.C1C(=O)N([Br:44])C(=O)C1.O.CCCCCC.C1(C)C=CC=CC=1>CN(C=O)C>[Br:44][C:20]1[CH:19]=[C:18]([C:27]2[CH:36]=[CH:35][C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[CH:28]=2)[C:17]2[C:26]3=[C:25]4[C:14]([CH:13]=[CH:12][C:11]([C:2]5[CH:3]=[CH:4][C:5]6[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=6)[CH:1]=5)=[C:24]4[CH:23]=[CH:22][C:21]=13)=[CH:15][CH:16]=2

Participants

6

Reactant 4

HCID 962WaterHCID 67184N-bromobutanimideHCID 21889329Toluene hexaneHCID 59795539HCID 59795539, compound

Product 1

HCID 86606381HCID 86606381, compoundYield 90.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

8.0 g of 1,6-dinaphthalene-2-yl-pyrene prepared by a well known method was dispersed into 80 ml of DMF, and 3.2 g of NBS in DMF solution was dropped therein at room temperature. After 3 days reaction, 150 ml of water was added to it and the deposited crystal was filtrated, followed by water and ethanol washing of the crystal. The crystal obtained was refined through a silica gel chromatography (a developing solvent: hexane/toluene=2/1) and then 8.5 g of 3-bromo-1,6-dinaphthalene-2-yl-pyrene was obtained as the intermediate (the yield: 90%). 8.5 g of 3-bromo-1,6-dinaphthalene-2-yl-pyrene obtained and 2.3 g of phenyl boronic acid were dissolved in 100 ml of DME. Subsequently, 0.55 g of tetrakistriphenylphosphinepalladium and 25 ml of 2M-sodium carbonate aqueous solution were added therein, followed by argon displacement. After heating and refluxing over 8 hours, it was stood to cool, and then the deposited crystal was filtrated. After washing the crystal by water and methanol, it was refined through a silica gel chromatography (a developing solvent: toluene), and then 5.4 g of 1,6-dinaphthalene-2-yl-3-phenylpyrene of the light-yellow crystalline was obtained (the yield: 64%).

Workup

  1. additionwas dropped
  2. customat room temperature
  3. additionwas added to it
  4. filtrationthe deposited crystal was filtrated
  5. washwashing of the crystal
  6. customThe crystal obtained

Sources & evidence

ORD record
ord-f6ee341b978349b3b278f79e5f124e64
Source dataset
uspto-grants-2012_11
Patent number
US08318995B2

Reaction notes

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