Sodium Dithionite → 5-(4-Amino-2,6-dibromo-3-methylphenoxy)-2-hydroxy-3-isopropylbenzaldehyde

HRID 1392554Notes

Reaction equation

HRID 1392554 reaction equation
[Br:1][C:2]1[C:20]([CH3:21])=[C:19]([N+:22]([O-])=O)[CH:18]=[C:17]([Br:25])[C:3]=1[O:4][C:5]1[CH:6]=[C:7]([CH:14]([CH3:16])[CH3:15])[C:8]([OH:13])=[C:9]([CH:12]=1)[CH:10]=[O:11].[O-]S(S([O-])=O)=O.[Na+].[Na+].C([O-])(O)=O.[Na+]>C(O)C>[NH2:22][C:19]1[CH:18]=[C:17]([Br:25])[C:3]([O:4][C:5]2[CH:6]=[C:7]([CH:14]([CH3:16])[CH3:15])[C:8]([OH:13])=[C:9]([CH:12]=2)[CH:10]=[O:11])=[C:2]([Br:1])[C:20]=1[CH3:21]

Participants

5

Reactant 3

HCID 24489Sodium DithioniteHCID 516892Sodium Bicarbonate2×HCID 596784105-(2,6-Dibromo-3-methyl-4-nitrophenoxy)-2-hydroxy-3-isopropylbenzaldehyde

Product 1

HCID 596784095-(4-Amino-2,6-dibromo-3-methylphenoxy)-2-hydroxy-3-isopropylbenzaldehydeYield 27%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-(2,6-Dibromo-3-methyl-4-nitrophenoxy)-2-hydroxy-3-isopropylbenzaldehyde of Part 8D (100 mg, 0.21 mmol), Na2S2O4 (553 mg, 3.2 mmol), NaHCO3 (0.2 mL, saturated aqueous solution) and ethanol (1.8 mL) were mixed in a microwave safe reaction vial. The vial was sealed and irradiated for 5 minutes at 140° C. NaHCO3 (5 mL, saturated aqueous solution) was added to the reaction mixture and the organic phase removed in vacuo. The obtained suspension was extracted with CHCl3 and the two phases were separated with phase separator (IST). The organic phase was concentrated and filtration through a pad of silica gave 25 mg (27%) of 5-(4-amino-2,6-dibromo-3-methylphenoxy)-2-hydroxy-3-isopropylbenzaldehyde as white foam.

Workup

  1. customThe vial was sealed
  2. customirradiated for 5 minutes at 140° C
  3. customthe organic phase removed in vacuo
  4. extractionThe obtained suspension was extracted with CHCl3
  5. customthe two phases were separated with phase separator (IST)
  6. concentrationThe organic phase was concentrated
  7. filtrationfiltration through a pad of silica

Sources & evidence

ORD record
ord-98336c3ab9e043ed939fd5d1b970024b
Source dataset
uspto-grants-2008_03
Patent number
US07342127B2

Reaction notes

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