Boron tribromide → HCID 13228938, compound

HRID 1380550Notes

Reaction equation

HRID 1380550 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:5]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18]C)=[C:14]([CH3:20])[CH:13]=2)[C:6]=1[CH2:7][C:8]([OH:10])=[O:9].B(Br)(Br)Br>ClCCl>[Cl:1][C:2]1[N:3]=[C:4]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:5]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[C:14]([CH3:20])[CH:13]=2)[C:6]=1[CH2:7][C:8]([OH:10])=[O:9]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 12822158HCID 12822158, compound

Product 1

HCID 13228938HCID 13228938, compoundYield 75.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-Chloro-1-(4-methoxy-3-methylbenzyl)-2-phenylimidazole-5-acetic acid (1.1 g) was suspended in 20 ml of dichloromethane and 4 ml of a dichloromethane solution containing 1 g of boron tribromide was added dropwise under stirring at room temperature. A precipitate separated out immediately after dissolution of the starting material. The mixture was allowed to stand for 6 hours. The supernatant was discarded and the precipitate was stirred with 50 ml each of ethyl acetate and water. The ethyl acetate layer was washed with water and evaporated to dryness under reduced pressure. The residue was washed with a small amount of acetone and recrystallized from aqueous alcohl to give 0.8 g of 4-chloro-1-(4-hydroxy-3-methylbenzyl)-2-phenylimidazole-5-acetic acid as colorless scales, m.p. 193°-195° C. (decompn.).

Workup

  1. additionwas added dropwise
  2. customA precipitate separated out immediately
  3. dissolutionafter dissolution of the starting material
  4. stirringthe precipitate was stirred with 50 ml each of ethyl acetate and water
  5. washThe ethyl acetate layer was washed with water
  6. customevaporated to dryness under reduced pressure
  7. washThe residue was washed with a small amount of acetone
  8. customrecrystallized from aqueous alcohl

Sources & evidence

ORD record
ord-846a5116c6eb427587a31c3866916234
Source dataset
uspto-grants-1986_04
Patent number
US04582847

Reaction notes

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