Boron tribromide → HCID 58156773, compound

HRID 2172160Notes

Reaction equation

HRID 2172160 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:9]2[O:13][C:12](=[O:14])[N:11]([C:15]3[CH:24]=[CH:23][C:18]([C:19]([O:21]C)=[O:20])=[CH:17][CH:16]=3)[N:10]=2)[CH:6]=[CH:7][CH:8]=1)#[N:2].B(Br)(Br)Br>ClCCl>[C:1]([C:3]1[CH:4]=[C:5]([C:9]2[O:13][C:12](=[O:14])[N:11]([C:15]3[CH:24]=[CH:23][C:18]([C:19]([OH:21])=[O:20])=[CH:17][CH:16]=3)[N:10]=2)[CH:6]=[CH:7][CH:8]=1)#[N:2]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 66616156HCID 66616156, compound

Product 1

HCID 58156773HCID 58156773, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl 4-[5-(3-cyanophenyl)-2-oxo-1,3,4-oxadiazol-3(2H)-yl]benzoate (0.60 g, 1.87 mmol) is then treated with boron tribromide (1M in dichloromethane, 5.6 mL, 5.6 mmol) in dichloromethane (20 mL) at room temperature overnight. The volatiles are removed in vacuum and the residue is treated with water. The crude product is separated by column chromatography (silica gel, 1:9 methanol-dichloromethane) to furnish the desired product, 4-[5-(3-cyanophenyl)-2-oxo-1,3,4-oxadiazol-3(2H)-yl]benzoic acid (0.46 g, 81%). m.p. 294-295° C. (decomp.). 1H NMR (CDCl3, 300 MHz) δ (ppm) 7.47 (t, 1H), 7.77 (d, 2H), 7.88-8.00 (m, 4H). (ES+) m/z: 307.

Workup

  1. customThe volatiles are removed in vacuum
  2. additionthe residue is treated with water
  3. customThe crude product is separated by column chromatography (silica gel, 1:9 methanol-dichloromethane)

Sources & evidence

ORD record
ord-b226fa06e11b4a0ca944a6749000d342
Source dataset
uspto-grants-2015_06
Patent number
US09051342B2

Reaction notes

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