Cyanocyclobutane → 1-(4-Bromo-2-iodobenzyl)cyclobutanecarbonitrile

HRID 539285노트

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HRID 539285 반응식
C([N-]C(C)C)(C)C.[Li+].[CH:9]1([C:13]#[N:14])[CH2:12][CH2:11][CH2:10]1.[Br:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22]Br)=[C:18]([I:24])[CH:17]=1>C1COCC1>[Br:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][C:9]2([C:13]#[N:14])[CH2:12][CH2:11][CH2:10]2)=[C:18]([I:24])[CH:17]=1

참가 물질

5

반응물 3

HCID 78148CyanocyclobutaneHCID 2724682Lithium diisopropylamideHCID 532313074-Bromo-1-(bromomethyl)-2-iodobenzene

생성물 1

HCID 679794311-(4-Bromo-2-iodobenzyl)cyclobutanecarbonitrile수율 89%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
-78 °C

실험 절차

Lithium diisopropylamide (3.34 mL, 6.68 mmol), was added dropwise to a solution of cyclobutanecarbonitrile (0.417 g, 5.14 mmol) in THF (20 mL) at −78° C. under an argon atmosphere. The reaction mixture was stirred at −78° C. for 30 min, then was a solution of 4-bromo-1-(bromomethyl)-2-iodobenzene (see Caruso, A.; Tovar, J., D. J. Org. Chem. 2011, 76, 2227-2239, 2.51 g, 6.68 mmol) in THF (8 mL) slowly added dropwise and the reaction was allowed to reach r.t. The mixture was stirred for another 3 h and then quenched with water. The reaction mixture was partitioned between water and EtOAc, the organic layer was dried over MgSO4 and concentrated to give a crude product which was purified by flash chromatography (eluent: heptane/ethylacetae 12:1) to afford the title compound (1.71 g, 89% yield): 1H NMR (500 MHz, CDCl3) δ ppm 2.08-2.34 (m, 4 H), 2.47-2.58 (m, 2 H), 3.18-3.23 (m, 2 H), 7.29 (s, 1 H), 7.49 (dd, 1 H), 8.03 (d, 1 H); GC MS (EI) m/z 375 M+.

후처리

  1. customto reach r.t
  2. stirringThe mixture was stirred for another 3 h
  3. customquenched with water
  4. customThe reaction mixture was partitioned between water and EtOAc
  5. dry with materialthe organic layer was dried over MgSO4
  6. concentrationconcentrated
  7. customto give a crude product which
  8. customwas purified by flash chromatography (eluent: heptane/ethylacetae 12:1)

출처 및 근거

ORD 기록
ord-45c60eafe1c34111aad8ad94835235df
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08865911B2

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