Bromobenzene → HCID 14822341, compound

HRID 1756125Notes

Reaction equation

HRID 1756125 reaction equation
[Mg].Br[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:9]([N:16]1[C:20]([CH2:21][CH2:22][CH2:23][C:24]([O:26]CC)=O)=[CH:19][N:18]=[CH:17]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[Cl-].[NH4+]>O1CCCC1>[CH2:9]([N:16]1[C:20]([CH2:21][CH2:22][CH2:23][C:24]([OH:26])([C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)=[CH:19][N:18]=[CH:17]1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 7961BromobenzeneHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 19916877HCID 19916877, compound

Product 1

HCID 14822341HCID 14822341, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

Magnesium turnings (0,49 g) are covered with 4 ml of dry tetrahydrofuran. Brombenzene (3,18 g) in 7 ml of dry tetrahydrofuran is added dropwise to the mixture at such a rate that a smooth reaction is maintained. The reaction mixture is refluxed for an additional hour. Ethyl 4-(1-benzyl-1H-imidazol-5-yl)butyrate (1,10 g) in 15 ml of dry tetrahydrofuran is then added dropwise to the Grignard reagent and the reaction mixture is refluxed for 2 hours. Saturated ammonium chloride is added to the cooled reaction mixture. Tetrahydrofuran is evaporated and the precipitated product is collected. Yield 1,41 g. Melting point of the hydrochloride salt is 197°-201° C.

Workup

  1. customthat a smooth reaction
  2. temperatureis maintained
  3. temperatureThe reaction mixture is refluxed for an additional hour
  4. temperaturethe reaction mixture is refluxed for 2 hours
  5. customTetrahydrofuran is evaporated
  6. customthe precipitated product is collected
  7. customis 197°-201° C.

Sources & evidence

ORD record
ord-b1cc8f13393d4c8b84d6268a02274e41
Source dataset
uspto-grants-1995_08
Patent number
US05439928

Reaction notes

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