Sodium Sulfite → (S)-1-(2-Bromo-6-methyl-4-nitrophenyl)ethane-1,2-diol

HRID 1468706ノート

反応式

HRID 1468706 の反応式
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4](C)[C:3]=1C=C.CS(N)(=O)=O.[O-]S([O-])=O.[Na+].[Na+].[C:25]([OH:29])(C)([CH3:27])[CH3:26].[OH2:30]>>[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([CH3:3])[C:26]=1[C@H:25]([OH:29])[CH2:27][OH:30]

参加物

5

反応物 4

HCID 24437Sodium SulfiteHCID 72879MethanesulfonamideHCID 714019492-Methylpropan-2-ol--water (1/1)HCID 866997861-Bromo-3-methyl-5-nitro-2-vinylbenzene

生成物 1

HCID 70982486(S)-1-(2-Bromo-6-methyl-4-nitrophenyl)ethane-1,2-diol

反応条件

温度
0 °C

実験手順

The reaction mixture of 1-bromo-3-methyl-5-nitro-2-vinylbenzene (65C) (12.3 g, 50.83 mmol), AD-mix a (71 g), MeSO2NH2 (4.8 g, 50.8 mmol) in t-butyl alcohol/H2O (1:1) (200 ml) was stirred at 0° C. for 3 days. Na2SO3 (˜6 g) was added to quench the reaction, stirred at rt for 40 min. The reaction mixture was washed by water, extracted by EtOAc, dry over MgSO4, filtered, concentrated down and purified by silica gel column, eluting by 0-100% EtOAc in Hexanes to give 6.96 g of 65D and recovered 2.3 g of 65C.

後処理

  1. customto quench
  2. customthe reaction
  3. stirringstirred at rt for 40 min
  4. washThe reaction mixture was washed by water
  5. extractionextracted by EtOAc
  6. dry with materialdry over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated down
  9. custompurified by silica gel column
  10. washeluting by 0-100% EtOAc in Hexanes

出典と根拠

ORDレコード
ord-d7a666588dbb4dfe89ac180cbf046cc6
出典データセット
uspto-grants-2015_04
特許番号
US09006229B2

反応ノート

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