Sodium Bicarbonate → 4-Iodo-2-nitrobenzaldehyde

HRID 1499639ノート

反応式

HRID 1499639 の反応式
[C:1]([O-:4])(O)=O.[Na+].BrC[C:8]1[CH:13]=[CH:12][C:11]([I:14])=[CH:10][C:9]=1[N+:15]([O-:17])=[O:16]>CS(C)=O.O>[I:14][C:11]1[CH:12]=[CH:13][C:8]([CH:1]=[O:4])=[C:9]([N+:15]([O-:17])=[O:16])[CH:10]=1

参加物

5

反応物 2

HCID 516892Sodium BicarbonateHCID 179660241-(Bromomethyl)-4-iodo-2-nitrobenzene

生成物 1

HCID 215327854-Iodo-2-nitrobenzaldehyde収率 61%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒

反応条件

温度
86 °C

実験手順

NaHCO3 (3.32 g, 39.48 mmol) was added to a solution of 1-bromomethyl-4-iodo-2-nitrobenzene (2.25 g, 6.58 mmol) in anhydrous DMSO (150 mL). The mixture was stirred at 86° C. for 19 hours under a nitrogen atmosphere, then cooled down to room temperature, diluted with water (300 mL), and extracted with methylene chloride four times (250 mL). The combined organic phase was dried over Na2SO4, concentrated in vacuo, and purified by silica gel chromatography to yield 4-iodo-2-nitrobenzaldehyde (1.11 g, 61%). 1H NMR (400 MHz, CDCl3): δ 10.38 (d, 1 H, J=1.6 Hz, CHO), 8.45 (d, 1 H, J=1.5 Hz, Ph-H), 8.15 (dd, 1 H, J=1.5 and 8.0 Hz, Ph-H), 7.67 (d, 1 H, J=8.1 Hz, Ph-H); 13C NMR (100 MHz, CDCl3): δ 187.28 (CH), 143.18 (CH), 133.29 (CH), 130.67 (CH), 130.28 (C), 109.60 (C), 99.78 (C).

後処理

  1. temperaturecooled down to room temperature
  2. extractionextracted with methylene chloride four times (250 mL)
  3. dry with materialThe combined organic phase was dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. custompurified by silica gel chromatography

出典と根拠

ORDレコード
ord-53cca578b29743108766a72a0608e1e7
出典データセット
uspto-grants-2015_12
特許番号
US09200319B2

反応ノート

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