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

HRID 1468706Notes

Reaction equation

HRID 1468706 reaction equation
[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]

Participants

5

Reactant 4

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

Product 1

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

Conditions

Temperature
0 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-d7a666588dbb4dfe89ac180cbf046cc6
Source dataset
uspto-grants-2015_04
Patent number
US09006229B2

Reaction notes

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