Ethyl bromoacetate → Ethyl 2-(4-bromo-2-nitrophenoxy)acetate

HRID 570152ノート

反応式

HRID 570152 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21]>CN(C)C=O>[CH2:23]([O:22][C:20](=[O:21])[CH2:19][O:8][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][C:4]=1[N+:9]([O-:11])=[O:10])[CH3:24]

参加物

5

反応物 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 243644-Bromo-2-nitrophenol

生成物 1

HCID 24903547Ethyl 2-(4-bromo-2-nitrophenoxy)acetate収率 77%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

To a solution of 4-bromo-2-nitro-phenol (3.28 g, 15.0 mmol, 1 equiv) in dimethylformamide (40 mL) at 23° C. was added potassium carbonate (4.14 g, 30 mmol, 2 equiv) followed by ethyl bromoacetate (1.84 mL, 16.6 mmol, 1.1 equiv). The resulting mixture was warmed to 60° C. (oil bath) for 90 min then cooled to 23° C. The reaction mixture was partitioned between ethyl acetate:heptane (1:1) and water (100 mL each). The organic layer was separated and washed successively with water, saturated brine solution (100 ml, each) then dried (MgSO4), filtered and concentrated to give 4.50 g (11.5 mmol, 77%) of the product as a yellow oil.

後処理

  1. temperaturethen cooled to 23° C
  2. customThe reaction mixture was partitioned between ethyl acetate:heptane (1:1) and water (100 mL each)
  3. customThe organic layer was separated
  4. washwashed successively with water, saturated brine solution (100 ml
  5. dry with materialeach) then dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-92a8b32be51c464ba385f2f4b6fddb48
出典データセット
uspto-grants-2015_05
特許番号
US09023843B2

反応ノート

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