Diethyl Oxalate → Ethyl 2-(5-bromo-2-(methoxymethoxy)phenyl)-2-oxoacetate

HRID 931554

반응식

HRID 931554 반응식
Br[C:2]1[CH:7]=[C:6]([Br:8])[CH:5]=[CH:4][C:3]=1[O:9][CH2:10][O:11][CH3:12].[Li]CCCC.[C:18](OCC)(=[O:24])[C:19]([O:21][CH2:22][CH3:23])=[O:20]>CCOCC>[Br:8][C:6]1[CH:5]=[CH:4][C:3]([O:9][CH2:10][O:11][CH3:12])=[C:2]([C:18](=[O:24])[C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:7]=1

참가 물질

5

반응물 3

HCID 7268Diethyl OxalateHCID 105658332,4-Dibromo-1-(methoxymethoxy)benzeneHCID 178418339Butyllithium

생성물 1

HCID 57475646Ethyl 2-(5-bromo-2-(methoxymethoxy)phenyl)-2-oxoacetate수율 112.8%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

실험 절차

A solution of 2,4-dibromo-1-(methoxymethoxy)benzene (40.5 g, 137 mmol) in Et2O (140 mL) was cooled to −78° C. and treated with n-BuLi (2.5M in hexanes; 60.2 mL, 151 mmol) under nitrogen atmosphere. After 30 minutes a solution of diethyl oxalate (27.9 mL, 205 mmol) in Et2O (20 mL) was added dropwise. The reaction mixture was stirred for 45 minutes at that temperature then quenched cold with saturated ammonium chloride solution. The mixture was partitioned between Et2O and water. The organic phase was separated, washed with water, brine, then dried over MgSO4. The solvent was removed under reduced pressure to afford 49 g of ethyl 2-(5-bromo-2-(methoxymethoxy)phenyl)-2-oxoacetate, which was used in the next step without further purification.

후처리

  1. customthen quenched cold with saturated ammonium chloride solution
  2. customThe mixture was partitioned between Et2O and water
  3. customThe organic phase was separated
  4. washwashed with water, brine
  5. dry with materialdried over MgSO4
  6. customThe solvent was removed under reduced pressure

출처 및 근거

ORD 기록
ord-c7ab1c04844b4cb88af2589c7e2f8f95
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09296759B2

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