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

HRID 503907노트

반응식

HRID 503907 반응식
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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-28c08f19384c47e49eed3747fdb5069b
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07776910B2

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