Triethylamine → HCID 90314138, 화합물

HRID 1505750

반응식

HRID 1505750 반응식
Br[C:2]1[CH:3]=[CH:4][C:5]([Cl:13])=[C:6]([CH:12]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8].[CH:14]1([C:17]#[CH:18])[CH2:16][CH2:15]1.C(N(CC)CC)C>CN(C=O)C.C1(C)C=CC=CC=1.[Cu](I)I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:13][C:5]1[CH:4]=[CH:3][C:2]([C:18]#[C:17][CH:14]2[CH2:16][CH2:15]2)=[CH:12][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8]

참가 물질

8

반응물 3

HCID 8471TriethylamineHCID 138823CyclopropylacetyleneHCID 144749Ethyl 5-bromo-2-chlorobenzoate

생성물 1

HCID 90314138HCID 90314138, 화합물수율 103.7%

시약·촉매·용매 4

HCID 83717Copper iodide촉매HCID 178418476HCID 178418476, 화합물촉매HCID 1140Toluene용매HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

To a solution of ethyl 5-bromo-2-chlorobenzoate (1.9 g) in DMF (12 mL), toluene (0.3 mL), cyclopropylacetylene (714 mg), copper iodide (275 mg), dichloro bis(triphenylphosphine)palladium (1.01 g) and triethylamine (20.1 mL) were added, and the mixture was degassed, stirred at 100° C. under argon atmosphere for 8 hours, and then the reaction mixture was cooled to room temperature and diluted with ethyl acetate. The insoluble material was filtered off on celite. The mother liquor was washed with brine, dried over magnesium sulfate and concentrated. By purification on column chromatography, ethyl 2-chloro-5-(cyclopropylethynyl)benzoate (1.86 g) was obtained as brown oil.

후처리

  1. customthe mixture was degassed
  2. temperaturethe reaction mixture was cooled to room temperature
  3. additiondiluted with ethyl acetate
  4. filtrationThe insoluble material was filtered off on celite
  5. washThe mother liquor was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated
  8. customBy purification on column chromatography

출처 및 근거

ORD 기록
ord-560e49dc0ade4467833eb5257c93f891
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09216968B2

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