m-Chloroperbenzoic acid → HCID 13187947, compound

HRID 1905760Notes

Reaction equation

HRID 1905760 reaction equation
[Cl:1][C:2]1([Cl:13])[CH:7]2[CH2:8][CH:4]([CH:5]=[CH:6]2)[C:3]1([C:11]#[N:12])[C:9]#[N:10].ClC1C=CC=C(C(OO)=[O:22])C=1.S(=O)(O)[O-].[Na+]>ClC1C=CC=CC=1>[Cl:1][C:2]1([Cl:13])[CH:7]2[CH2:8][CH:4]([CH:5]3[O:22][CH:6]32)[C:3]1([C:9]#[N:10])[C:11]#[N:12]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 12930698HCID 12930698, compoundHCID 23665763Sodium Bisulfite

Product 1

HCID 13187947HCID 13187947, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent2×

Procedure

21 g (0.1 mol) of the (IV) prepared in Example 1 are dissolved in 100 ml of chlorobenzene, and 20 g (0.12 mol) of m-chloroperbenzoic acid in 200 ml of chlorobenzene are added dropwise. The mixture is heated under reflux for 4 hours, and is worked up in the customary manner with sodium bisulphite solution to destroy the excess of per-acid, and sodium bicarbonate solution to separate off the m-chlorobenzoic acid. From the organic phase, 17 g (75%) of 3,3-dichloro-5,6-epoxybicyclo[2,2,1]heptane-2,2-dicarbonitrile were isolated, m.p. 229° C.

Workup

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for 4 hours
  3. customto destroy the excess of per-acid, and sodium bicarbonate solution
  4. customto separate off the m-chlorobenzoic acid

Sources & evidence

ORD record
ord-58e6eb43527e452e92c46d0fd931a279
Source dataset
uspto-grants-1987_03
Patent number
US04647581

Reaction notes

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