m-Chloroperbenzoic acid → HCID 66875337, compound

HRID 1259066Notes

Reaction equation

HRID 1259066 reaction equation
[Br:1][C:2]1[C:3]([C:8]#[N:9])=[N:4][CH:5]=[CH:6][CH:7]=1.ClC1C=CC=C(C(OO)=[O:18])C=1>C(Cl)(Cl)Cl>[Br:1][C:2]1[C:3]([C:8]#[N:9])=[N+:4]([O-:18])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 8176943-Bromopyridine-2-carbonitrile

Product 1

HCID 66875337HCID 66875337, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 3-bromopicolinonitrile (1.0 eq.) in chloroform (0.3 M) was added 77% meta-chloroperbenzoic acid (mCPBA) (1.8 eq.) and heated at 60° C. for 2 days. After cooling to room temperature, Ca(OH)2 (2.5 eq.) was added, and the resulting precipitate was stirred for 30 minutes. The precipitate was filtered and washed with 5% methanol in dichloromethane. The filtrate was washed with saturated aqueous NaHCO3 solution. The aqueous layer was extracted several times with 3% methanol in dichloromethane. The combined organic layers were dried over anhydrous MgSO4 and concentrated en vacuo. The crude product was stirred in hot hexane/ethyl acetate (1:1), filtered, and dried to give the desired product as a white solid.

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationThe precipitate was filtered
  3. washwashed with 5% methanol in dichloromethane
  4. washThe filtrate was washed with saturated aqueous NaHCO3 solution
  5. extractionThe aqueous layer was extracted several times with 3% methanol in dichloromethane
  6. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  7. concentrationconcentrated en vacuo
  8. stirringThe crude product was stirred in hot hexane/ethyl acetate (1:1)
  9. filtrationfiltered
  10. customdried

Sources & evidence

ORD record
ord-905cb3a807bf425587cc8c97ffdba06f
Source dataset
uspto-grants-2013_06
Patent number
US08466167B2

Reaction notes

Loading…