Boron tribromide → HCID 23347387, compound

HRID 1856010Notes

Reaction equation

HRID 1856010 reaction equation
[CH2:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([O:13]C)=[CH:10][CH:11]=2)[C:6]([CH2:15][N:16]2[CH:20]=[CH:19][N:18]=[CH:17]2)=[CH:5]1)[CH:2]=[CH2:3].B(Br)(Br)Br>>[CH2:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([OH:13])=[CH:10][CH:11]=2)[C:6]([CH2:15][N:16]2[CH:20]=[CH:19][N:18]=[CH:17]2)=[CH:5]1)[CH:2]=[CH2:3]

Participants

3

Reactant 2

HCID 25134Boron tribromideHCID 23347423HCID 23347423, compound

Product 1

HCID 23347387HCID 23347387, compoundYield 44.1%

Procedure

The procedure described in Example XLVII was repeated except that 1-allyl-3-(imidazol-1-ylmethyl)-5-methoxyindole (1.34 g.) and boron tribromide (1.91 ml.) were the reactant and reagent respectively employed under these same conditions. After basification with sodium bicarbonate, the aqueous layer was extracted with three-100 ml. portions of ethyl acetate and the combined organic extracts were washed with water and subsequently dried over anhydrous magnesium sulfate. Evaporation of the solvent then gave a solid product, which later was crystallized from ethanol to afford pure 1-allyl-5-hydroxy-3-(imidazol-1-ylmethyl)indole (yield, 0.56 g.), m.p. 165°-167° C.

Workup

  1. extractionAfter basification with sodium bicarbonate, the aqueous layer was extracted with three-100 ml
  2. washportions of ethyl acetate and the combined organic extracts were washed with water
  3. dry with materialsubsequently dried over anhydrous magnesium sulfate
  4. customEvaporation of the solvent
  5. customthen gave a solid product, which
  6. customlater was crystallized from ethanol

Sources & evidence

ORD record
ord-faa2aa9c657e440eab0d76dd7b7ccf60
Source dataset
uspto-grants-1980_08
Patent number
US04217357

Reaction notes

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