Hydrochloric Acid → HCID 87806978, compound

HRID 860975Notes

Reaction equation

HRID 860975 reaction equation
C1N2CN3CN(C2)CN1C3.[CH3:11][O:12][C:13](=[O:31])[CH2:14][C:15]1[CH:20]=[C:19]([Br:21])[C:18]([O:22][C:23]2[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=2)=[C:17]([Br:30])[CH:16]=1.FC(F)(F)[C:34](O)=[O:35].Cl>>[CH3:11][O:12][C:13](=[O:31])[CH2:14][C:15]1[CH:20]=[C:19]([Br:21])[C:18]([O:22][C:23]2[CH:28]=[CH:27][C:26]([OH:29])=[C:25]([CH:34]=[O:35])[CH:24]=2)=[C:17]([Br:30])[CH:16]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 4101HexamethylenetetramineHCID 6422Trifluoroacetic acidHCID 69384135Methyl [3,5-dibromo-4-(4-hydroxyphenoxy)phenyl]acetate

Product 1

HCID 87806978HCID 87806978, compoundYield 38%

Conditions

Temperature
95 °C

Procedure

Hexamethylenetetramine (262 mg, 1.87 mmol) was added to a solution of methyl[3,5-dibromo-4-(4-hydroxyphenoxy)phenyl]acetate (370 mg, 0.89 mmol) and trifluoroacetic acid (1.5 mL). The reaction mixture was stirred for 16 hours at 95° C. before cooling to room temperature. Hydrochloric acid (3 mL, 2 N) was added and the reaction mixture was stirred for one hour and extracted with chloroform. The organic phase was concentrated in vacuo and dissolved in ethyl acetate. The organic phase was washed with hydrochloric acid (2 N), water and brine, dried over Na2SO4 and concentrated. The residue was purified on a column (MPLC, silica, gradient eluent: n-heptane/ethyl acetate from 1:0 to 4:1) to give yielded methyl[3,5-dibromo-4-(3-formyl-4-hydroxyphenoxy)phenyl]acetate as a white solid (150 mg, 38%).

Workup

  1. temperaturebefore cooling to room temperature
  2. stirringthe reaction mixture was stirred for one hour
  3. extractionextracted with chloroform
  4. concentrationThe organic phase was concentrated in vacuo
  5. dissolutiondissolved in ethyl acetate
  6. washThe organic phase was washed with hydrochloric acid (2 N), water and brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated
  9. customThe residue was purified on a column (MPLC, silica, gradient eluent: n-heptane/ethyl acetate from 1:0 to 4:1)
  10. customto give

Sources & evidence

ORD record
ord-4f8d571a69064c7a85e83308f9c1a10a
Source dataset
uspto-grants-2006_12
Patent number
US07153997B2

Reaction notes

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