1-Chloro-4-iodobenzene → HCID 11623195, 화합물

HRID 522514

반응식

HRID 522514 반응식
[S:1]1[CH:5]=[C:4]([CH:6]=[O:7])[C:3]2[CH:8]=[CH:9][CH:10]=[CH:11][C:2]1=2.[Li+].[Cl-].[Cl:14][C:15]1[CH:20]=[CH:19][C:18](I)=[CH:17][CH:16]=1>C1COCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd]>[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([C:5]2[S:1][C:2]3[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=3[C:4]=2[CH:6]=[O:7])=[CH:17][CH:16]=1

참가 물질

6

반응물 3

HCID 125101-Chloro-4-iodobenzeneHCID 2273281-Benzothiophene-3-carbaldehydeHCID 433294Lithium Chloride

생성물 1

HCID 11623195HCID 11623195, 화합물수율 87%

시약·촉매·용매 2

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium촉매HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
25 °C

실험 절차

Benzo[b]thiophene-3-carbaldehyde (27) (162 mg, 1.0 mmol) in THF (2 mL) was added to a solution of TMPZnCl.LiCl (2) (1.3 M in THF, 0.85 mL, 1.1 mmol) at 25° C. and the reaction mixture was then stirred at this temperature for 30 min according to TP 2. Pd(dba)2 (17 mg, 3 mol %) and P(o-furyl)3 (14 mg, 6 mol %) dissolved in THF (2 mL), and mixed with 1-chloro-4-iodobenzene (310 mg, 1.3 mmol, 1.3 equiv) were then transferred via cannula to the reaction mixture. The resulting mixture was stirred for 2 h at 25° C. The reaction mixture was then quenched with a sat. aq. NH4Cl solution (20 mL), extracted with diethyl ether (3×50 mL) and dried over anhydrous Na2SO4. After filtration, the solvent was evaporated in vacuo. Purification by flash-chromatography (CH2Cl2/n-pentane, 1:3) furnished compound 29b (236 mg, 87%) as a colourless solid.

후처리

  1. customThe reaction mixture was then quenched with a sat. aq. NH4Cl solution (20 mL)
  2. extractionextracted with diethyl ether (3×50 mL)
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationAfter filtration
  5. customthe solvent was evaporated in vacuo
  6. customPurification by flash-chromatography (CH2Cl2/n-pentane, 1:3)

출처 및 근거

ORD 기록
ord-726a5057ea6d4016b726d656ff0db3a7
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09334237B2

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