Triethylamine → 3-[[3-(Trifluoromethoxy)phenyl]ethynyl]aniline

HRID 1030866노트

반응식

HRID 1030866 반응식
[F:1][C:2]([O:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8](Br)[CH:7]=1)([F:4])[F:3].C(N(CC)CC)C.[NH2:20][C:21]1[CH:22]=[C:23]([C:27]#[CH:28])[CH:24]=[CH:25][CH:26]=1>CCOCC.[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>[F:1][C:2]([F:4])([F:3])[O:5][C:6]1[CH:7]=[C:8]([C:28]#[C:27][C:23]2[CH:22]=[C:21]([CH:26]=[CH:25][CH:24]=2)[NH2:20])[CH:9]=[CH:10][CH:11]=1

참가 물질

7

반응물 3

HCID 8471TriethylamineHCID 104682Benzenamine, 3-ethynyl-HCID 5199641-Bromo-3-(trifluoromethoxy)benzene

생성물 1

HCID 198210813-[[3-(Trifluoromethoxy)phenyl]ethynyl]aniline수율 86%

시약·촉매·용매 3

HCID 11776Triphenylphosphine촉매HCID 10122028Bis(triphenylphosphine)palladium촉매HCID 3283Diethyl Ether용매

반응 조건

온도
65 °C

실험 절차

A multinecked flask as described in Example 1 was charged with 5.0 g (0.021 mol) of m-bromophenyl trifluoromethyl ether, 50 ml of dried, degassed triethylamine, 2.43 g (0.212 mol) of 3-aminophenylacetylene, 0.048 g (0.68 mmol) of bis(triphenylphosphine) palladium II chloride, 0.148 g (0.564 mmol) of triphenylphosphine, and 0.03 g (0.157 mmol) of cuprous iodide. The reaction mixture was heated at 65° C. for 20 hours at which point gas chromotography showed the reaction to be complete. The product mixture was cooled to room temperature and diluted with 75 ml of ether. Filtration of the insoluble triethylamine hydrobromide salt by-product followed by concentration of the filtrate gave the crude product as a viscous orange-colored liquid. Short path distillation of the crude product under reduced pressure gave 5.1 g (0.018 mol, 86% yield) of the purified product as a colorless liquid.

후처리

  1. customA multinecked flask as described in Example 1
  2. customof dried
  3. customthe reaction
  4. temperatureThe product mixture was cooled to room temperature
  5. filtrationFiltration of the insoluble triethylamine hydrobromide salt by-product
  6. customgave the crude product as a viscous orange-colored liquid
  7. distillationShort path distillation of the crude product under reduced pressure

출처 및 근거

ORD 기록
ord-060fe6916ebc47eaa012245b39deec3d
출처 데이터셋
uspto-grants-1992_04
특허 번호
US05107026

반응 노트

불러오는 중…