Trimethylsilylacetylene → 1,4-Dichloro-2-ethynylbenzene

HRID 59264

반응식

HRID 59264 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1I.[C:10]([Si](C)(C)C)#[CH:11].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>[Cu](I)I.[Pd](Cl)Cl.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.C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[C:10]#[CH:11]

참가 물질

7

반응물 3

HCID 66111TrimethylsilylacetyleneHCID 1224521,4-Dichloro-2-iodobenzeneHCID 2724141Tetrabutylammonium Fluoride

생성물 1

HCID 126397541,4-Dichloro-2-ethynylbenzene수율 89.3%

시약·촉매·용매 3

HCID 83717Copper iodide촉매HCID 6102075Dichlorobis(triphenylphosphine)palladium촉매HCID 6344Dichloromethane용매

실험 절차

The title compound was prepared according to the procedure described in step-5 and step-6 of Intermediate-2 by using 1,4-dichloro-2-iodobenzene (1.0 g, 3.6 mmol), ethynyl(trimethyl)silane (0.541 g, 5.5 mmol), copper iodide (0.027 g, 0.14 mmol), bis(triphenylphosphine) palladium(II) chloride (0.050 g, 0.072 mmol), TBAF (catalytic) and DCM to afford 0.550 g of desired product. 1H NMR (300 MHz, DMSO d6): δ 4.73 (s, 1H), 7.50 (d, J=8.7 Hz, 1H), 7.58 (d, J=8.7 Hz, 1H), 7.71 (s, 1H).

후처리

  1. customThe title compound was prepared

출처 및 근거

ORD 기록
ord-190e1ea3be0d4cb89996a786f02a2774
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09439890B2

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