Potassium Phosphate, Tribasic → 9,10-Bis(1,2,3,4-tetrahydro-1,4-methanonaphth-5-yl)anthracene

HRID 1190774

反応式

HRID 1190774 の反応式
C1(P(C2CCCCC2)C2(OC)[CH2:13][CH:12]=[CH:11][C:10](OC)=[C:9]2[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)CCCCC1.Br[C:31]1[C:32]2[C:37]([C:38](Br)=[C:39]3[C:44]=1[CH:43]=[CH:42][CH:41]=[CH:40]3)=[CH:36][CH:35]=[CH:34][CH:33]=2.[CH:46]12[CH2:59][CH:49]([C:50]3[C:51](B(O)O)=[CH:52][CH:53]=[CH:54][C:55]=31)[CH2:48][CH2:47]2.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.O>[CH:46]12[CH2:59][CH:49]([C:50]3[C:55]1=[CH:54][CH:53]=[CH:52][C:51]=3[C:31]1[C:32]3[C:37]([C:38]([C:21]4[CH:20]=[CH:19][CH:18]=[C:17]5[C:16]=4[CH:9]4[CH2:10][CH:11]5[CH2:12][CH2:13]4)=[C:39]4[C:44]=1[CH:43]=[CH:42][CH:41]=[CH:40]4)=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH2:48][CH2:47]2

参加物

7

反応物 4

HCID 62657Potassium Phosphate, TribasicHCID 682269,10-DibromoanthraceneHCID 576945921,2,3,4-Tetrahydro-1,4-methanonaphthalene-5-boronic AcidHCID 665453372-Dicyclohexylphosphino-2,6-dimethoxybiphenyl

生成物 1

HCID 576946619,10-Bis(1,2,3,4-tetrahydro-1,4-methanonaphth-5-yl)anthracene

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 1140Toluene溶媒

実験手順

915 my (1 mmol) of tris(dibenzylidenacetone)dipalladium(0) and 821 mg (2 mmol) of 2-dicyclohexylphosphino-2,6-dimethoxybiphenyl are added to a suspension of 16.8 g (50 mmol) of 9,10-dibromoanthracene, 21.6 g (115 mol) of 1,2,3,4-tetrahydro-1,4-methanonaphthalene-5-boronic acid and 66.9 g (315 mmol) of tripotassium phosphate in 400 ml of anhydrous toluene, and the mixture is refluxed for 16 h. After the reaction mixture has been cooled, 400 ml of water are added, and the precipitate is filtered off with suction, washed three times with 200 ml of water each time, washed three times with 200 ml of ethanol each time, dried under reduced pressure and subsequently chromatographed on silica gel (eluent heptane/toluene 8:2, v/v, column temperature 500C). Sublimation: p=1×10−5 mbar, 300° C. Yield: 13.1 g (28 mmol), 56.6% of theory; purity: 99.5% according to 1H-NMR (including all isomers).

後処理

  1. temperaturethe mixture is refluxed for 16 h
  2. temperatureAfter the reaction mixture has been cooled
  3. filtrationthe precipitate is filtered off with suction
  4. washwashed three times with 200 ml of water each time
  5. washwashed three times with 200 ml of ethanol each time
  6. customdried under reduced pressure
  7. customsubsequently chromatographed on silica gel (eluent heptane/toluene 8:2, v/v, column temperature 500C)
  8. customp=1×10−5 mbar, 300° C

出典と根拠

ORDレコード
ord-8b5ecce045a94954bbbd1177d97df5e4
出典データセット
uspto-grants-2014_03
特許番号
US08679645B2

関連ノート

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