N-bromobutanimide → HCID 18692940, compound

HRID 1957244Notes

Reaction equation

HRID 1957244 reaction equation
[Cl:1][C:2]1[C:3]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([CH2:19]C(Cl)C(OC)=O)[CH:13]=2)=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[Br:26]N1C(=O)CCC1=O>ClC(Cl)(Cl)Cl>[Br:26][CH2:19][C:14]1[CH:13]=[C:12]([C:3]2[C:2]([Cl:1])=[CH:7][C:6]([C:8]([F:11])([F:10])[F:9])=[CH:5][N:4]=2)[CH:17]=[CH:16][C:15]=1[Cl:18]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 19068790HCID 19068790, compound

Product 1

HCID 18692940HCID 18692940, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of 9.6 g (31.4 mmol) of 3-chloro-2-(4-chloro-3-methylphenyl)5-trifluoromethylpyridine (prepared as in Example 16) and 5.6 g (31.5 mmol) of N-bromosuccinimide in 150 ml of tetrachloromethane was irradiated with a 150 W high-pressure Hg lamp for one hour. For the workup, the precipitated succinimide was removed, and the filtrate was concentrated under reduced pressure. The residue was taken up in cyclohexane. The solids were removed and discarded, and the cyclohexane solution was concentrated again. The crude product was purified by chromatography on silica gel (mobile phase: n-pentane/methyl tert-butyl ether 20:1). Yield: 6.2 g (51%) of colorless crystals of melting point 71°-72° C.

Workup

  1. customFor the workup, the precipitated succinimide was removed
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe solids were removed
  4. concentrationthe cyclohexane solution was concentrated again
  5. customThe crude product was purified by chromatography on silica gel (mobile phase: n-pentane/methyl tert-butyl ether 20:1)

Sources & evidence

ORD record
ord-dad9dcc58b9a49058818d01f771525e9
Source dataset
uspto-grants-1998_07
Patent number
US05783522

Reaction notes

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