Heptane → HCID 69388013, compound

HRID 860968Notes

Reaction equation

HRID 860968 reaction equation
[CH3:1][O:2][C:3](=[O:28])[CH2:4][C:5]1[CH:10]=[C:9]([Br:11])[C:8]([O:12][C:13]2[CH:18]=[C:17]([CH:19]([CH3:21])[CH3:20])[C:16]([O:22][CH3:23])=[C:15]([N+:24]([O-])=O)[CH:14]=2)=[C:7]([Br:27])[CH:6]=1.S(S([O-])=O)([O-])=O.[Na+].[Na+].CCCCCCC>C(O)C.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:28])[CH2:4][C:5]1[CH:10]=[C:9]([Br:11])[C:8]([O:12][C:13]2[CH:18]=[C:17]([CH:19]([CH3:21])[CH3:20])[C:16]([O:22][CH3:23])=[C:15]([NH2:24])[CH:14]=2)=[C:7]([Br:27])[CH:6]=1

Participants

6

Reactant 3

HCID 8900HeptaneHCID 24489Sodium DithioniteHCID 69386549HCID 69386549, compound

Product 1

HCID 69388013HCID 69388013, compoundYield 44.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

Methyl[3,5-dibromo-4-(5-isopropyl-4-methoxy-3-nitrophenoxy)phenyl]acetate (1.1 g, 2.12 mmol) was dissolved in ethanol (50 mL) and sodium hydrosulfite (1.85 g, 10.6 mmol) was added. The reaction mixture was heated at reflux for 48 hours. The reaction monitored by TLC (65:35 n-heptane: EtOAc) and when complete, diluted with ethyl acetate and washed with water and brine. The organic layer was dried over MgSO4 and concentrated. The residue was purified on column (silica gel, n-heptane/EtOAc 1:1) to yield methyl[3,5-dibromo-4-(3-amino-5-isopropyl-4-methoxyphenoxy)phenyl]acetate (457 mg, 44%).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 48 hours
  3. washwashed with water and brine
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified on column (silica gel, n-heptane/EtOAc 1:1)

Sources & evidence

ORD record
ord-d0e6c11ee7bd4b75ad0dd7b8713d83c6
Source dataset
uspto-grants-2006_12
Patent number
US07153997B2

Reaction notes

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