Toluene → Ethyl 4-iodo-2-methanesulfonylbenzoate

HRID 2411152ノート

反応式

HRID 2411152 の反応式
Br[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[C:4]([S:13]([CH3:16])(=[O:15])=[O:14])[CH:3]=1.[I-:17].[Na+].C1(C)C=CC=CC=1.CNCCNC>[Cu]I.O>[I:17][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[C:4]([S:13]([CH3:16])(=[O:15])=[O:14])[CH:3]=1

参加物

7

反応物 4

HCID 1140TolueneHCID 5238Sodium IodideHCID 8070N,N'-DimethylethylenediamineHCID 59251585Ethyl 4-bromo-2-(methanesulfonyl)benzoate

生成物 1

HCID 71252507Ethyl 4-iodo-2-methanesulfonylbenzoate収率 64.5%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 962Water溶媒

実験手順

To a mixture of ethyl 4-bromo-2-methanesulfonylbenzoate (13.88 g), sodium iodide (13.54 g) and copper(I) iodide (4.30% g) were added toluene (46 mL) and N,N′-dimethylethylenediamine (4.86 mL), and the mixture was stirred with heating under reflux for 8 hr under a nitrogen stream. The reaction mixture was cooled, water was added, and the mixture was extracted with ethyl acetate. The solvent was evaporated from the organic layer, the obtained residue was purified by column chromatography (hexane:ethyl acetate) to give ethyl 4-iodo-2-methanesulfonylbenzoate (10.32 g). To a mixture of the obtained ethyl 4-iodo-2-methanesulfonylbenzoate (3.22 g), (R)-3-methylisothiazolidine 1,1-dioxide (1.23 g) described in Preparation Example 2, copper(I) iodide (4.30 g), N,N′-dimethylethylenediamine (0.92 mL) and potassium carbonate (2.52 g) was added toluene (9.2 mL), and the mixture was stirred with heating under reflux for 8 hr under a nitrogen stream. The reaction mixture was cooled, water was added, and the mixture was extracted with ethyl acetate. The solvent was evaporated from the organic layer, and the obtained residue was purified by column chromatography (hexane:ethyl acetate) to give the title compound (1.7 g).

後処理

  1. temperaturewith heating
  2. temperatureunder reflux for 8 hr under a nitrogen stream
  3. temperatureThe reaction mixture was cooled
  4. extractionthe mixture was extracted with ethyl acetate
  5. customThe solvent was evaporated from the organic layer
  6. customthe obtained residue was purified by column chromatography (hexane:ethyl acetate)

出典と根拠

ORDレコード
ord-605a6b12b5d6475eb141675965b2cbbd
出典データセット
uspto-grants-2014_08
特許番号
US08816079B2

反応ノート

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