Ammonium Chloride → 3-(4-Bromo-2-methyl-phenyl)-3-cyano-propionic acid methyl ester

HRID 503907ノート

反応式

HRID 503907 の反応式
C([N-]C(C)C)(C)C.[Li+].[Br:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][C:17]#[N:18])=[C:12]([CH3:19])[CH:11]=1.Br[CH2:21][C:22]([O:24][CH3:25])=[O:23].[NH4+].[Cl-]>C1COCC1.O>[CH3:25][O:24][C:22](=[O:23])[CH2:21][CH:16]([C:13]1[CH:14]=[CH:15][C:10]([Br:9])=[CH:11][C:12]=1[CH3:19])[C:17]#[N:18]

参加物

7

反応物 4

HCID 25517Ammonium ChlorideHCID 60984Methyl bromoacetateHCID 2724682Lithium diisopropylamideHCID 184142962-(4-Bromo-2-methylphenyl)acetonitrile

生成物 1

HCID 668771313-(4-Bromo-2-methyl-phenyl)-3-cyano-propionic acid methyl ester収率 83.2%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

Lithium diisopropylamide (2 M in THF, 110 mL) was added dropwise at −78° C. to a solution of (4-bromo-2-methyl-phenyl)-acetonitrile (38.55 g, 0.1835 mol) in THF (400 mL). The reaction mixture was stirred for 10 minutes and methyl bromoacetate (16.87 mL, 0.1835 mol) was added. The resulting mixture was stirred at −78° C. for 2 hours. A saturated solution of NH4Cl was then added at −78° C. and the resulting mixture was warmed to room temperature. Water was added and the mixture was extracted with EtOAc. The combined organic extracts were washed with water and brine; dried over MgSO4, filtered, and evaporated under reduced pressure. The residue was purified via flash chromatography (hexane/EtOAc, 9/1) to give 43.09 g of 3-(4-bromo-2-methyl-phenyl)-3-cyano-propionic acid methyl ester (83% yield) as a yellow oil.

後処理

  1. stirringThe resulting mixture was stirred at −78° C. for 2 hours
  2. extractionthe mixture was extracted with EtOAc
  3. washThe combined organic extracts were washed with water and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe residue was purified via flash chromatography (hexane/EtOAc, 9/1)

出典と根拠

ORDレコード
ord-28c08f19384c47e49eed3747fdb5069b
出典データセット
uspto-grants-2010_08
特許番号
US07776910B2

反応ノート

読み込み中…