5-Bromosalicylaldehyde → 2-Hydroxy-5-(methanesulfonyl)benzaldehyde

HRID 1810457ノート

反応式

HRID 1810457 の反応式
Br[C:2]1[CH:9]=[C:6]([CH:7]=[O:8])[C:5]([OH:10])=[CH:4][CH:3]=1.[CH3:11][S:12]([O-:14])=[O:13].[Na+]>CN1C(=O)CCC1.CCOC(C)=O.[Cu]I>[OH:10][C:5]1[CH:4]=[CH:3][C:2]([S:12]([CH3:11])(=[O:14])=[O:13])=[CH:9][C:6]=1[CH:7]=[O:8]

参加物

6

反応物 2

HCID 728635-BromosalicylaldehydeHCID 2733271Sodium methanesulfinate

生成物 1

HCID 574198652-Hydroxy-5-(methanesulfonyl)benzaldehyde

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 8857Ethyl Acetate溶媒HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
140 °C

実験手順

5-Bromosalicylaldehyde (0.402 g, 2.0 mmol), sodium methanesulfinate (0.918 g, 9.0 mmol), and copper(I) iodide (1.71 g, 9.0 mmol) were combined in NMP (16 mL) and stirred under N2 at 140° C. overnight. The mixture was diluted with 1:1 EtOAc:hexanes (150 mL) and filtered through a pad of Celite. The filtrate was washed three times with H2O, and then dried, filtered, and concentrated. The residue was purified by silica gel chromatography (0-100% EtOAc in hexanes) to give the title compound.

後処理

  1. filtrationhexanes (150 mL) and filtered through a pad of Celite
  2. washThe filtrate was washed three times with H2O
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography (0-100% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-c11852579c6642c8b121e43edf4f9728
出典データセット
uspto-grants-2013_01
特許番号
US08362044B2

反応ノート

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