Hydrochloric Acid → 3-Iodo-5-(methoxycarbonyl)benzoic acid

HRID 14291

反応式

HRID 14291 の反応式
N[C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([C:11]([O:13][CH3:14])=[O:12])[CH:10]=1)[C:5]([OH:7])=[O:6].Cl.N([O-])=O.[Na+].[I-:20].[K+]>O>[I:20][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([C:11]([O:13][CH3:14])=[O:12])[CH:10]=1)[C:5]([OH:7])=[O:6]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 135576433-Amino-5-(methoxycarbonyl)benzoic acidHCID 23668193Sodium Nitrite

生成物 1

HCID 158403913-Iodo-5-(methoxycarbonyl)benzoic acid収率 55.1%

試薬・触媒・溶媒 1

HCID 962Water溶媒3 回

実験手順

To an ice-cold, stirred solution of 3-amino-5-(methoxycarbonyl)benzoic acid (5.19 g, 26.59 mmol) in a 2 N hydrochloric acid (156 mL) was added a solution of sodium nitrite (1.84 g, 26.67 mmol) in water (10.8 mL). This mixture was then added dropwise to an ice-cold, stirred solution of potassium iodide (8.84 g, 53.25 mmol) in water (26.2 mL). After stirring for 35 min, the reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with 5% aqueous sodium thiosulfate, and saturated sodium chloride, dried (sodium sulfate), and concentrated under reduced pressure. Purification by flash column chromatography (silica, 50:50:2 hexanes/ethyl acetate/acetic acid) afforded 3-iodo-5-(methoxycarbonyl)benzoic acid (4.48 g): 1H NMR (500 MHz, DMSO-d6): δ 13.49 (br s, 1H), 8.45-8.38 (m, 3H), 3.83 (s, 3H); ESI-MS (m/z): 305 [M+H]+.

後処理

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with 5% aqueous sodium thiosulfate, and saturated sodium chloride
  3. dry with materialdried (sodium sulfate)
  4. concentrationconcentrated under reduced pressure
  5. customPurification by flash column chromatography (silica, 50:50:2 hexanes/ethyl acetate/acetic acid)

出典と根拠

ORDレコード
ord-b9e365e738df4d5f94ed7d7af91e7e2d
出典データセット
uspto-grants-2010_06
特許番号
US07727997B2

関連ノート

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