Water → HCID 178520566, compound

HRID 1756134Notes

Reaction equation

HRID 1756134 reaction equation
[Mg].Br[C:3]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][CH:4]=1.[O:10]=[C:11]([C:22]1[N:23]=[CH:24][NH:25][CH:26]=1)[CH2:12][CH2:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.O>O1CCCC1>[F:9][C:6]1[CH:7]=[CH:8][C:3]([C:11]([C:22]2[N:23]=[CH:24][NH:25][CH:26]=2)([OH:10])[CH2:12][CH2:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:4][CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 99931-Bromo-4-fluorobenzeneHCID 5462224MagnesiumHCID 178520567HCID 178520567, compound

Product 1

HCID 178520566HCID 178520566, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

0,52 g of magnesium turnings are covered with 60 ml of dry tetrahydrofuran. Then a solution of 1-bromo-4-fluorobenzene (3,8 g) in 60 ml of dry tetrahydrofuran is added dropwise to the mixture at such a rate that a smooth reaction is maintained. After the addition is complete, the reaction mixture is refluxed for one additional hour and cooled to room temperature. The reaction mixture is then added dropwise to a solution of 4-(1-oxo-5-phenylpentyl)-1H-imidazole (3,8 g) in 40 ml of tetrahydrofuran at 60° C. After the addition is complete, the reaction mixture is refluxed for 3 hours, cooled and poured into cold water. Tetrahydrofuran is evaporated and conc. hydrochloric acid is added to the solution. The product is extracted as hydrochloric salt into methylene chloride. Combined methylene chloride extracts are then evaporated to dryness.

Workup

  1. customthat a smooth reaction
  2. temperatureis maintained
  3. additionAfter the addition
  4. temperaturethe reaction mixture is refluxed for one additional hour
  5. additionAfter the addition
  6. temperaturethe reaction mixture is refluxed for 3 hours
  7. temperaturecooled
  8. customTetrahydrofuran is evaporated
  9. additionconc. hydrochloric acid is added to the solution
  10. extractionThe product is extracted as hydrochloric salt into methylene chloride
  11. customCombined methylene chloride extracts are then evaporated to dryness

Sources & evidence

ORD record
ord-7c08209a1c9342b8b43d0fdb04785f5b
Source dataset
uspto-grants-1995_08
Patent number
US05439928

Reaction notes

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