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Toluene → HCID 59489285, 화합물

HRID 385309
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HRID 385309 반응식
FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]2[CH:30]=[CH:29][C:28]3[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[C:15]=3[CH:14]=2)[CH:8]=1)(=O)=O.[CH3:33][O:34][C:35]1[CH:36]=[C:37](B(O)O)[CH:38]=[CH:39][CH:40]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C1(C)C=CC=CC=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.O>[CH3:33][O:34][C:35]1[CH:36]=[C:37]([C:11]2[CH:12]=[CH:7][CH:8]=[C:9]([C:13]3[CH:30]=[CH:29][C:28]4[C:27]5[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=5)[C:21]5[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=5)[C:15]=4[CH:14]=3)[CH:10]=2)[CH:38]=[CH:39][CH:40]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 1140TolueneHCID 62657Potassium Phosphate, TribasicHCID 2734370(3-Methoxyphenyl)boronic acidHCID 592458333-(Triphenylen-2-yl)phenyl trifluoromethanesulfonate

생성물 1

HCID 59489285HCID 59489285, 화합물수율 98.2%

시약·촉매·용매 3

HCID 9811564
Bis(dibenzylideneacetone)palladium
촉매
HCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl촉매
HCID 962Water용매

실험 절차

12.9 g (28.5 mmol) 3-(triphenylen-2-yl)phenyl trifluoromethanesulfonate, 6.5 g (42.8 mmol) 3-methoxyphenylboronic acid, 0.47 g (1.1 mmol) 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (SPhos) and 18.2 g (85.5 mmol) potassium phosphate tribasic (K3PO4) were weighed in a round bottom flask. 150 mL toluene and 80 mL water were added to the flask as solvent. The solution was purged with nitrogen and 0.26 g (0.28 mmol) of tris(dibenzylideneacetone)dipalladium (0) [Pd2(dba)3] was added. The solution was heated to reflux for twelve hours. Upon cooling, the organic layer was separated, and dried with MgSO4. The product was readily separated by column chromatography using hexane/dichloromethane as eluent (1/0 gradient to 3/2). The solvent was removed by rotary evaporation resulting in 11.7 g (28 mmol) of the product, 2-(3′-methoxybiphenyl-3-yl)triphonylene.

후처리

  1. additionwas added
  2. temperatureThe solution was heated
  3. temperatureto reflux for twelve hours
  4. temperatureUpon cooling
  5. customthe organic layer was separated
  6. dry with materialdried with MgSO4
  7. customThe product was readily separated by column chromatography
  8. customThe solvent was removed by rotary evaporation

출처 및 근거

ORD 기록
ord-543217797b774adf9fa7e0b7986b10ff
출처 데이터셋
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08367850B2

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