Hydrogen Bromide → 1-(2-fluoro-4-hydroxyphenyl)-1,4-dihydro-4-(3-fluoropropyl)-5H-tetrazol-5-one

HRID 482402Notes

Reaction equation

HRID 482402 reaction equation
FC1C=CC(C[O:9][C:10]2[CH:15]=[CH:14][C:13]([N:16]3[C:20](=[O:21])[N:19]([CH2:22][CH2:23][CH2:24][F:25])[N:18]=[N:17]3)=[C:12]([F:26])[CH:11]=2)=CC=1.Br>C(O)(=O)C>[F:26][C:12]1[CH:11]=[C:10]([OH:9])[CH:15]=[CH:14][C:13]=1[N:16]1[C:20](=[O:21])[N:19]([CH2:22][CH2:23][CH2:24][F:25])[N:18]=[N:17]1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 189810431-[4-(4-fluorophenylmethoxy)-2-fluorophenyl]-1,4-dihydro-4-(3-fluoropropyl)-5H-tetrazol-5-one

Product 1

HCID 189810471-(2-fluoro-4-hydroxyphenyl)-1,4-dihydro-4-(3-fluoropropyl)-5H-tetrazol-5-oneYield 111%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 5.60 g (0.0153 mole) of 1-[4-(4-fluorophenylmethoxy)-2-fluorophenyl]-1,4-dihydro-4-(3-fluoropropyl)-5H-tetrazol-5-one in 60 mL of glacial acetic acid was added 5 mL of 49% hydrobromic acid. This mixture was heated at reflux for 90 minutes, after which it was cooled to room temperature. The reaction mixture was then poured over ice, and the resulting aqueous solution was extracted with diethyl ether. The combined extract was dried over magnesium sulfate, filtered, and the solvent was evaporated under reduced pressure, leaving 4.35 g of 1-(2-fluoro-4-hydroxy-phenyl)-1,4-dihydro-4-(3-fluoropropyl)-5H-tetrazol-5-one as a residue.

Workup

  1. temperatureThis mixture was heated
  2. temperatureat reflux for 90 minutes
  3. additionThe reaction mixture was then poured over ice
  4. extractionthe resulting aqueous solution was extracted with diethyl ether
  5. extractionThe combined extract
  6. dry with materialwas dried over magnesium sulfate
  7. filtrationfiltered
  8. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-4117a6207fa64e4f80c6e8a865350241
Source dataset
uspto-grants-1998_08
Patent number
US05798316

Reaction notes

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