Boron trifluoride etherate → HCID 71743722、化合物

HRID 2277634ノート

反応式

HRID 2277634 の反応式
[Br:1][C:2]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][C:3]=1[C:4]#[N:5].[CH3:11][CH2:12][Mg+].[Br-].B(F)(F)F.CCOCC>C1COCC1>[Br:1][C:2]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][C:3]=1[C:4]1([NH2:5])[CH2:12][CH2:11]1

参加物

5

反応物 3

HCID 8000Boron trifluoride etherateHCID 103309442-Bromo-5-chlorobenzonitrileHCID 178461630HCID 178461630、化合物

生成物 1

HCID 71743722HCID 71743722、化合物収率 17.6%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirred solution of 2-bromo-5-chlorobenzonitrile (10 g, 46 mmol) and Ti(Oi-Pr)4 (16.64 mL, 55 mmol) in THF (200 mL) at −78° C. was added EtMgBr (138 mL, 138 mmol) dropwise. The reaction mixture was allowed to warm up to room temperature and stirred for 2 hours. BF3-Et2O (17.2 mL) was added, and the solution was stirred for another 16 hours before it was quenched with aq. HCl solution and washed with EtOAc. The aqueous phase was adjusted to pH˜10 with aq. NaOH solution, and exacted with EtOAc (3×). The combined organic layers were concentrated to give a crude product which was purified by chromatography to afford title compound (2 g, yield 17.6%). MS: 246.7 (M+H+, 1C1) as oil.

後処理

  1. stirringthe solution was stirred for another 16 hours before it
  2. customwas quenched with aq. HCl solution
  3. washwashed with EtOAc
  4. concentrationThe combined organic layers were concentrated
  5. customto give a crude product which
  6. customwas purified by chromatography

出典と根拠

ORDレコード
ord-4d1c1e48f3d64b2d84f15e6f0d85ab15
出典データセット
uspto-grants-2015_09
特許番号
US09133158B2

反応ノート

読み込み中…