Chlorosuccinimide → 5-Chloro-2-ethoxybenzoic acid

HRID 78477

反応式

HRID 78477 の反応式
[CH2:1]([O:3][C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7])[CH3:2].[Cl:13]N1C(=O)CCC1=O>C(#N)C>[Cl:13][C:10]1[CH:11]=[CH:12][C:4]([O:3][CH2:1][CH3:2])=[C:5]([CH:9]=1)[C:6]([OH:8])=[O:7]

参加物

4

反応物 2

HCID 31398ChlorosuccinimideHCID 672522-Ethoxybenzoic acid

生成物 1

HCID 50985705-Chloro-2-ethoxybenzoic acid

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒2 回

実験手順

To a solution of 2-ethoxybenzoic acid (4.4 g, 26.6 mmol) in 80 mL of acetonitrile at 0° C. was added N-chlorosuccinimide (3.7 g, 28 mmol) in 20 mL of acetonitrile dropwise over 30 minutes. The reaction mixture was warmed to ambient temperature and the mixture was allowed to stir for 70 hours. The mixture was quenched with 20 mL of H2O and the layers were separated. The aqueous layer was extracted with three 15 mL portions of CH2Cl2 and the combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. Purification via recrystallization with ether and hexanes afforded the title compound. MS (DCI/NH3) m/z 201 (M+H)+, 218 (M+NH4)+.

後処理

  1. customThe mixture was quenched with 20 mL of H2O
  2. customthe layers were separated
  3. extractionThe aqueous layer was extracted with three 15 mL portions of CH2Cl2
  4. dry with materialthe combined organic extracts were dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification
  8. customvia recrystallization with ether and hexanes

出典と根拠

ORDレコード
ord-029cf09010894e74b3ccb96a99e26c5d
出典データセット
uspto-grants-2014_09
特許番号
US08841334B2

関連ノート

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