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

HRID 931554

反応式

HRID 931554 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c7ab1c04844b4cb88af2589c7e2f8f95
出典データセット
uspto-grants-2016_03
特許番号
US09296759B2

関連ノート

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