Water → HCID 23347379, compound

HRID 1856009Notes

Reaction equation

HRID 1856009 reaction equation
[N:1]1([CH2:6][C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([O:16]C)[CH:14]=3)[NH:9][CH:8]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.B(Br)(Br)Br.O.C(OCC)(=O)C>C(Cl)Cl>[OH:16][C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[C:7]2[CH2:6][N:1]1[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 25134Boron tribromideHCID 13594143HCID 13594143, compound

Product 1

HCID 23347379HCID 23347379, compoundYield 35.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

To a well-stirred solution consisting of 3-(imidazol-1-ylmethyl)-5-methoxyindole (0.30 g.) dissolved in dry methylene chloride (30 ml.) at -70° C., there was added boron tribromide (0.38 ml.) in a dropwise manner. The resulting mixture was allowed to warm up and was then stirred at 20° C. for a period of five hours. Water (50 ml.) was then added to the spent reaction mixture, and the resulting aqueous layer was subsequently separated and washed with methylene chloride (using two-20 ml. portions). The washed aqueous layer was then made basic with solid sodium bicarbonate and evaporated to dryness. The residue obtained in this manner was next treated with boiling ethyl acetate (200 ml.), and the resulting organic solution was separated from the mixture by decantation and then evaporated to give a solid. Crystallization of the latter material from isopropanol/petroleum ether (b.p. 80°-100° C.) then gave pure 5-hydroxy-3-(imidazol-1-ylmethyl)-indole (yield, 0.10 g.), m.p. 169°-170° C.

Workup

  1. temperatureto warm up
  2. customthe resulting aqueous layer was subsequently separated
  3. washwashed with methylene chloride (using two-20 ml. portions)
  4. customevaporated to dryness
  5. customThe residue obtained in this manner
  6. customthe resulting organic solution was separated from the mixture by decantation
  7. customevaporated
  8. customto give a solid
  9. customCrystallization of the latter material from isopropanol/petroleum ether (b.p. 80°-100° C.)

Sources & evidence

ORD record
ord-4a907927b71644f6b1e467564e3ffe4b
Source dataset
uspto-grants-1980_08
Patent number
US04217357

Reaction notes

Loading…