Sodium Iodide → 4-Iodomethyl benzoic acid tert-butyl ester

HRID 1401889ノート

反応式

HRID 1401889 の反応式
[I-:1].[Na+].[C:3]([O:7][C:8](=[O:17])[C:9]1[CH:14]=[CH:13][C:12]([CH2:15]Cl)=[CH:11][CH:10]=1)([CH3:6])([CH3:5])[CH3:4]>CC(C)=O>[C:3]([O:7][C:8](=[O:17])[C:9]1[CH:14]=[CH:13][C:12]([CH2:15][I:1])=[CH:11][CH:10]=1)([CH3:6])([CH3:5])[CH3:4]

参加物

4

反応物 2

HCID 5238Sodium IodideHCID 18959012tert-Butyl 4-(chloromethyl)benzoate

生成物 1

HCID 672121184-Iodomethyl benzoic acid tert-butyl ester収率 100%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

Sodium iodide (229.2 g) was added to a solution of 4-chloromethyl benzoic acid tert-butyl ester (315.2 g) in acetone (1.5 L). The reaction mixture was heated to reflux for about 2 h and then allowed to cool to room temperature. The precipitate was removed by filtration and the filtrate concentrated under reduced pressure. The residue was partitioned between water (500 mL) and MTBE (1500 mL). The organic phase was washed with saturated sodium bicarbonate and dried over magnesium sulfate. Concentration under reduced pressure afforded 442.2 g (97% yield) dark oil. HNMR: CDCl3, 1.59 ppm (s, 9H), 4.47 (s, 2H), 7.42 (d, 2H), 7.91 (d, 2H)

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for about 2 h
  3. customThe precipitate was removed by filtration
  4. concentrationthe filtrate concentrated under reduced pressure
  5. customThe residue was partitioned between water (500 mL) and MTBE (1500 mL)
  6. washThe organic phase was washed with saturated sodium bicarbonate
  7. dry with materialdried over magnesium sulfate
  8. concentrationConcentration under reduced pressure

出典と根拠

ORDレコード
ord-461521255155434faf7c67db3f319f13
出典データセット
uspto-grants-2014_12
特許番号
US08907103B2

反応ノート

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