Sodium Dithionite → 4-(4-Amino-2,6-dibromo-3-trifluoromethylphenoxy)-2-methyl-6-isopropylphenol

HRID 1392565Notes

Reaction equation

HRID 1392565 reaction equation
[Br:1][C:2]1[C:19]([C:20]([F:23])([F:22])[F:21])=[C:18]([N+:24]([O-])=O)[CH:17]=[C:16]([Br:27])[C:3]=1[O:4][C:5]1[CH:10]=[C:9]([CH:11]([CH3:13])[CH3:12])[C:8]([OH:14])=[C:7]([CH3:15])[CH:6]=1.S(S([O-])=O)([O-])=O.[Na+].[Na+].CCCCCCC.CCOC(C)=O>CCO.CCOC(C)=O>[NH2:24][C:18]1[CH:17]=[C:16]([Br:27])[C:3]([O:4][C:5]2[CH:10]=[C:9]([CH:11]([CH3:12])[CH3:13])[C:8]([OH:14])=[C:7]([CH3:15])[CH:6]=2)=[C:2]([Br:1])[C:19]=1[C:20]([F:23])([F:22])[F:21]

Participants

6

Reactant 3

HCID 24489Sodium DithioniteHCID 21899848Ethylacetate heptaneHCID 59678428HCID 59678428, compound

Product 1

HCID 596784334-(4-Amino-2,6-dibromo-3-trifluoromethylphenoxy)-2-methyl-6-isopropylphenolYield 81%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-(2,6-Dibromo-4-nitro-3-trifluoromethylphenoxy)-2-methyl-6-isopropylphenol of Part 11E (120 mg, 0.23 mmol) was dissolved in EtOH (5 mL) and sodium hydrosulfite (204 mg, 1.2 mmol) was added. The reaction mixture was heated at reflux for 48 hours. The reaction progress was monitored by TLC (n-heptane/EtOAc 65:35) and when complete diluted with EtOAc. The organic phase was washed with water, brine, dried over MgSO4 and concentrated. The residue was purified on column (silica gel, gradient elution with n-heptane/EtOAc) to give 90 mg (81%) of 4-(4-amino-2,6-dibromo-3-trifluoromethylphenoxy)-2-methyl-6-isopropylphenol.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 48 hours
  3. washThe organic phase was washed with water, brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified on column (silica gel, gradient elution with n-heptane/EtOAc)

Sources & evidence

ORD record
ord-9923ade478814a8c961ac6d67b469b3c
Source dataset
uspto-grants-2008_03
Patent number
US07342127B2

Reaction notes

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