Tetrahydrofuran → HCID 178509436, compound

HRID 530993Notes

Reaction equation

HRID 530993 reaction equation
[Br:1]N1C(=O)CCC1=O.[F:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[C:18]([OH:24])[N:17]=2)=[CH:12][CH:11]=1.C1COCC1>CO>[Br:1][C:23]1[C:16]([C:13]2[CH:14]=[CH:15][C:10]([F:9])=[CH:11][CH:12]=2)=[N:17][C:18]([OH:24])=[C:19]([CH:22]=1)[C:20]#[N:21]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 67184N-bromobutanimideHCID 178509569HCID 178509569, compound

Product 1

HCID 178509436HCID 178509436, compoundYield 94.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-Bromosuccinimide (3.66 g) was added to a mixture of 6-(4-fluorophenyl)-2-hydroxynicotinonitrile (4.00 g), THF (30 mL), and methanol (30 mL), and the resultant mixture was stirred at room temperature for 10 minutes. The solvent was distilled off, and the obtained residue was suspended in a mixed solvent of water, ethyl acetate, and hexane. Then, the obtained solid was washed with hexane to obtain the title compound (5.18 g).

Workup

  1. distillationThe solvent was distilled off
  2. washThen, the obtained solid was washed with hexane

Sources & evidence

ORD record
ord-f097f76f787c41c8bf71fc6b41d1ef70
Source dataset
uspto-grants-2016_05
Patent number
US09353108B2

Reaction notes

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