Sodium Dithionite → 4-(4-Amino-2,6-dibromo-3-methylphenoxy)-2-hydroxymethyl-6-isopropylphenol

HRID 1392560Notes

Reaction equation

HRID 1392560 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:10]=[C:9]([CH:11]([CH3:13])[CH3:12])[C:8]([OH:14])=[C:7]([CH2:15][OH:16])[CH:6]=1.[O-]S(S([O-])=O)=O.[Na+].[Na+].C([O-])(O)=O.[Na+]>CCO>[NH2:22][C:19]1[CH:18]=[C:17]([Br:25])[C:3]([O:4][C:5]2[CH:10]=[C:9]([CH:11]([CH3:13])[CH3:12])[C:8]([OH:14])=[C:7]([CH2:15][OH:16])[CH:6]=2)=[C:2]([Br:1])[C:20]=1[CH3:21]

Participants

5

Reactant 3

HCID 24489Sodium DithioniteHCID 516892Sodium BicarbonateHCID 596784304-(2,6-Dibromo-3-methyl-4-nitrophenoxy)-2-hydroxymethyl-6-isopropylphenol

Product 1

HCID 596784294-(4-Amino-2,6-dibromo-3-methylphenoxy)-2-hydroxymethyl-6-isopropylphenolYield 22%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of compound 4-(2,6-dibromo-3-methyl-4-nitrophenoxy)-2-hydroxymethyl-6-isopropylphenol of Part 10A (85 mg, 0.18 mmol), Na2S2O4 (467 mg, 2.68 mmol) and EtOH (2 mL) was prepared in a microwave safe reaction vial. After irradiation for 5 minutes at 170° C. a saturated aqueous solution of NaHCO3 (5 mL) was added to the reaction mixture. The organic phase was removed in vacuo and the aqueous phase was extracted with EtOAc and the organic phase was dried over Na2SO4. Concentration in vacuo gave a residue that was purified on column (silica gel, gradient elution: n-heptane/EtOAc from 1:0 to 7:3) to give 18 mg (22%) of 4-(4-amino-2,6-dibromo-3-methylphenoxy)-2-hydroxymethyl-6-isopropylphenol as a light yellow foam.

Workup

  1. customwas prepared in a microwave safe reaction vial
  2. additionwas added to the reaction mixture
  3. customThe organic phase was removed in vacuo
  4. extractionthe aqueous phase was extracted with EtOAc
  5. dry with materialthe organic phase was dried over Na2SO4
  6. concentrationConcentration in vacuo
  7. customgave a residue that
  8. customwas purified on column (silica gel, gradient elution: n-heptane/EtOAc from 1:0 to 7:3)

Sources & evidence

ORD record
ord-5549671e073b45bdb31191f92fe30d30
Source dataset
uspto-grants-2008_03
Patent number
US07342127B2

Reaction notes

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