Hydrochloric Acid → HCID 59678431, compound

HRID 1392563Notes

Reaction equation

HRID 1392563 reaction equation
[Br:1][C:2]1[C:18]([C:19]([F:22])([F:21])[F:20])=[C:17]([N+:23]([O-:25])=[O:24])[CH:16]=[C:15]([Br:26])[C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[C:7]([CH:12]([CH3:14])[CH3:13])[CH:6]=1.C1N2CN3CN(C2)CN1C3.Cl.[C:38](O)(C(F)(F)F)=[O:39]>>[Br:1][C:2]1[C:18]([C:19]([F:22])([F:21])[F:20])=[C:17]([N+:23]([O-:25])=[O:24])[CH:16]=[C:15]([Br:26])[C:3]=1[O:4][C:5]1[CH:6]=[C:7]([CH:12]([CH3:13])[CH3:14])[C:8]([OH:11])=[C:9]([CH:10]=1)[CH:38]=[O:39]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 4101HexamethylenetetramineHCID 6422Trifluoroacetic acidHCID 59678432HCID 59678432, compound

Product 1

HCID 59678431HCID 59678431, compoundYield 57%

Conditions

Temperature
98 °C

Procedure

4-(2,6-dibromo-4-nitro-3-trifluoromethylphenoxy)-2-isopropylphenol of Part 11C (220 mg, 0.44 mmol) was dissolved in TFA (3 mL) and hexamethylenetetramine (154 mg, 1.1 mmol) was added to the reaction. The reaction mixture was heated at 98° C. for 12 hours, cooled down and 1N HCl (4 mL) was added. The reaction mixture was stirred for 5 hours at room temperature, extracted with EtOAc, washed with H2O, NaHCO3 and brine. The organic layer was dried by MgSO4 and concentrated. The residue was purified on column (silica gel, gradient elution with n-heptane/EtOAc) to give 130 mg (57%) of 5-(2,6-dibromo-4-nitro-3-trifluoromethylphenoxy)-2-hydroxy-3-isopropylbenzaldehyde.

Workup

  1. temperaturecooled down
  2. extractionextracted with EtOAc
  3. washwashed with H2O, NaHCO3 and brine
  4. dry with materialThe organic layer was dried by MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified on column (silica gel, gradient elution with n-heptane/EtOAc)

Sources & evidence

ORD record
ord-842514a4470a4140bbd06dd57396660d
Source dataset
uspto-grants-2008_03
Patent number
US07342127B2

Reaction notes

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