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2,6-Lutidine → (E)-(2-bromomethyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)acetonitrile

HRID 452175
ノート
印刷プレビュー

反応式

HRID 452175 の反応式
C(C1N([CH2:14][C:15]2[CH:32]=[CH:31][C:18]3/[C:19](=[CH:28]/[C:29]#[N:30])/[C:20]4[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=4[CH2:22][CH2:23][C:17]=3[CH:16]=2)C2=NC(C)=CC(C)=C2N=1)C.N1C(C)=CC=CC=1C.[Br-:41].[Li+].CS(OS(C)(=O)=O)(=O)=O>C1COCC1.CCCCCC.C(OCC)(=O)C>[Br:41][CH2:14][C:15]1[CH:32]=[CH:31][C:18]2/[C:19](=[CH:28]/[C:29]#[N:30])/[C:20]3[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=3[CH2:22][CH2:23][C:17]=2[CH:16]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 79372,6-LutidineHCID 81560Methanesulfonic anhydrideHCID 82050Lithium BromideHCID 22858094(E)-[2-(2-ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridin-3-yl)methyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene]acetonitrile

生成物 1

HCID 67210773(E)-(2-bromomethyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)acetonitrile収率 74%

試薬・触媒・溶媒

3
HCID 8028Tetrahydrofuran溶媒HCID 8058Hexane溶媒HCID 8857Ethyl Acetate溶媒2 回

実験手順

(E)-(2-Hydroxymethyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)acetonitrile (JP-B-2526005; 10.00 g, 38.3 mmol) was dissolved in THF (380 mL), 2,6-lutidine (26.7 mL, 230 mmol), lithium bromide (19.94 g, 230 mmol) and methanesulfonic anhydride (16.67 g, 95.7 mmol) were added, and the mixture was stirred at room temperature for 16 hr. Ethyl acetate was added to the mixture, and the organic layer was washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give a residue. Ethyl acetate (10 mL) and hexane (5 mL) were added to the residue, and the mixture was filtered to give the title compound (9.18 g, 74%).

後処理

  1. washthe organic layer was washed with brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customto give a residue
  5. filtrationthe mixture was filtered

出典と根拠

ORDレコード
ord-ff35be1435ca45c3a63c7de1e1038fba
出典データセット
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08486980B2

反応ノート

読み込み中…

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