Sodium Carbonate → 9-(3-Bromophenyl)phenanthrene

HRID 1660662노트

반응식

HRID 1660662 반응식
[CH:1]1[C:14]2[CH:13]=[C:12](B(O)O)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[Br:18][C:19]1[CH:20]=[C:21](I)[CH:22]=[CH:23][CH:24]=1.C(=O)([O-])[O-].[Na+].[Na+]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O.C1(C)C=CC=CC=1.C(COC)OC>[Br:18][C:19]1[CH:24]=[C:23]([C:12]2[C:11]3[C:6]([C:5]4[CH:4]=[CH:3][CH:2]=[CH:1][C:14]=4[CH:13]=2)=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH:22]=[CH:21][CH:20]=1

참가 물질

8

반응물 3

HCID 10340Sodium CarbonateHCID 11561Benzene, 1-bromo-3-iodo-HCID 117757049-Phenanthracenylboronic acid

생성물 1

HCID 221380359-(3-Bromophenyl)phenanthrene수율 74%

시약·촉매·용매 4

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 962Water용매HCID 1140Toluene용매2회HCID 80711,2-Dimethoxyethane용매

실험 절차

Under an argon gas atmosphere, 31.4 g (141 mmol) of 9-phenanthreneboronic acid, 40.0 g (141 mmol) of 3-bromoiodobenzene, 3.30 g (2.83 mmol) of tetrakis(triphenylphosphine) palladium(0), 200 mL of toluene, 50 mL of dimethoxyethane and 212 mL of 2M sodium carbonate solution were mixed, and stirred for four hours while being refluxed. After the reaction, the reaction mixture was further added with toluene, and cleansed by water. After organic phase thereof was dried with magnesium sulfate, the toluene was distilled away under reduced pressure. Residue thereof was refined by silica-gel column chromatography, such that 34.7 g of 9-(3-bromophenyl)phenanthrene was obtained with an yield of 74%.

후처리

  1. temperaturewhile being refluxed
  2. customAfter the reaction
  3. dry with materialAfter organic phase thereof was dried with magnesium sulfate
  4. distillationthe toluene was distilled away under reduced pressure
  5. customwas obtained with an yield of 74%

출처 및 근거

ORD 기록
ord-63e0eabc98a344d391807e2e96190728
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08029697B2

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