Boron tribromide → HCID 22125759, compound

HRID 1858041Notes

Reaction equation

HRID 1858041 reaction equation
[N+:1]([C:4]1[C:9]([OH:10])=[C:8]([O:11]C)[CH:7]=[C:6]([N+:13]([O-:15])=[O:14])[C:5]=1[CH2:16][C:17]([OH:19])=[O:18])([O-:3])=[O:2].B(Br)(Br)Br>ClCCl>[OH:10][C:9]1[C:4]([N+:1]([O-:3])=[O:2])=[C:5]([CH2:16][C:17]([OH:19])=[O:18])[C:6]([N+:13]([O-:15])=[O:14])=[CH:7][C:8]=1[OH:11]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 54185805HCID 54185805, compound

Product 1

HCID 22125759HCID 22125759, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-20 °C

Procedure

The product from Example 3 (0.28 g) 3 was slurried in dichoromethane (15 ml), cooled to -20° C. and boron tribromide (0.4 ml) added under nitrogen. The reaction mixture was allowed to warm up to room temperature and then refluxed for four hours. The mixture was poured into ice-water and extracted to ethyl acetate. The product was purified by column chromatography using toluene-ethyl acetate-acetic acid 8:1:1 as the eluent. Yield: 21 mg, melting point 178-184° C.

Workup

  1. temperatureto warm up to room temperature
  2. temperaturerefluxed for four hours
  3. extractionextracted to ethyl acetate
  4. customThe product was purified by column chromatography

Sources & evidence

ORD record
ord-6d1f1476d7954de69aebc956278d576d
Source dataset
uspto-grants-2000_11
Patent number
US06150412

Reaction notes

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