Ethyl Acetate → HCID 66995360, compound

HRID 335181Notes

Reaction equation

HRID 335181 reaction equation
[NH2:1][C:2]1[C:7]([O:8][C:9]2[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][CH:10]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.[Br:17]Br.S(=O)(O)[O-].[Na+].C(OCC)(=O)C>C(O)(=O)C>[NH2:1][C:2]1[C:7]([O:8][C:9]2[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][CH:10]=2)=[CH:6][C:5]([Br:17])=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24408BromineHCID 23665763Sodium BisulfiteHCID 66994464HCID 66994464, compound

Product 1

HCID 66995360HCID 66995360, compoundYield 66.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
0 °C

Procedure

Placed 4-(2-aminopyridin-3-yloxy)benzonitrile (13.95 g, 66.05 mmol) in acetic acid (50 mL) and cooled to 0° C. Slowly added bromine (4.229 mL, 82.56 mmol) and stirred for an hour. The reaction mixture was poured onto saturated sodium bisulfite and ice. Extracted with dichloromethane three times, washed with 2N NaOH, water, brine, dried, and concentrated. Purified by MPLC eluting with 3:2 hexane:ethyl acetate to afford the title compound (12.7 g, 66.28% yield) as a light yellow solid.

Workup

  1. extractionExtracted with dichloromethane three times
  2. washwashed with 2N NaOH, water, brine
  3. customdried
  4. concentrationconcentrated
  5. customPurified by MPLC
  6. washeluting with 3:2 hexane

Sources & evidence

ORD record
ord-985e0aceb034479083ee37012664e692
Source dataset
uspto-grants-2014_11
Patent number
US08883828B2

Reaction notes

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