Toluene → 1,3-Bis[4-(phenylethynyl)phenyl]propan-2-one

HRID 1869063노트

반응식

HRID 1869063 반응식
BrC1C=CC([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH2:14][C:15](=[O:30])[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2C2C=CC(Br)=CC=2)=CC=1.[CH2:31](N(CC)CC)C.[C:38]1([C:44]#[CH:45])[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.CN(C)C=O.[C:51]1([CH3:57])[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>[C:38]1([C:44]#[C:45][C:20]2[CH:19]=[CH:18][C:17]([CH2:16][C:15](=[O:30])[CH2:14][C:9]3[CH:10]=[CH:11][C:12]([C:31]#[C:57][C:51]4[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=4)=[CH:13][CH:8]=3)=[CH:22][CH:21]=2)[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

참가 물질

9

반응물 5

HCID 1140TolueneHCID 6228DimethylformamideHCID 8471TriethylamineHCID 10821PhenylacetyleneHCID 67405464HCID 67405464, 화합물

생성물 1

HCID 579767661,3-Bis[4-(phenylethynyl)phenyl]propan-2-one

시약·촉매·용매 3

HCID 11776Triphenylphosphine촉매HCID 167845palladium(II) acetate촉매HCID 962Water용매

반응 조건

온도
80 °C

실험 절차

In a 250 ml flask was placed 18.4 grams (0.05 mole) of 1,3-bis-(4-bromophenylphenyl)-2-propanone, 24 grams (0.24 mole) of triethylamine, 12 grams (0.12 mole) of phenylacetylene, and 60 milliliters of N,N-dimethylformamide. The reaction mixture was purged with nitrogen for 15 minutes then 0.60 gram (0.0023 mole) of triphenylphosphine and 0.08 gram (0.00036 mole) of palladium acetate were added. After heating the reaction mixture at 80° C. under a nitrogen atmosphere for 20 hours, the flask was allowed to cool to room temperature, then water (200 milliliters) and toluene (200 milliliters) were added. The resulting organic layer was washed with 10% aqueous HCl, water and saturated aqueous NaCl then dried over anhydrous Na2SO4. The pure product (14.5 grams) was obtained upon removal of the toluene and recrystallization from toluene/hexanes in 71% isolated yield.

후처리

  1. customIn a 250 ml flask was placed
  2. customThe reaction mixture was purged with nitrogen for 15 minutes
  3. temperatureto cool to room temperature
  4. washThe resulting organic layer was washed with 10% aqueous HCl, water and saturated aqueous NaCl
  5. dry with materialthen dried over anhydrous Na2SO4

출처 및 근거

ORD 기록
ord-7375a48fdc554d3e839ffea8fc0ca4c2
출처 데이터셋
uspto-grants-2009_12
특허 번호
US07635741B2

반응 노트

불러오는 중…