Hydrogen Bromide → 3-Chloro-2-(4-chlorobenzyl)-5-trifluoromethylpyridine

HRID 1250145Notes

Reaction equation

HRID 1250145 reaction equation
[Cl:1][C:2]1[C:3]([CH:12]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)C#N)=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.Br>>[Cl:1][C:2]1[C:3]([CH2:12][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)=[N:4][CH:5]=[C:6]([C:8]([F:10])([F:11])[F:9])[CH:7]=1

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 27738272-(4-Chlorophenyl)-2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]acetonitrile

Product 1

HCID 183272763-Chloro-2-(4-chlorobenzyl)-5-trifluoromethylpyridine

Conditions

Temperature
23 °C

Procedure

4.3 g of 3-chloro-2-[1-(4-chlorophenyl)-1-cyanomethyl]-5-trifluoromethylpyridine (prepared by the method of Example 1) were heated under reflux in 50 ml of 47% strength aqueous hydrogen bromide solution for 3 hours and then stirred for another 68 hours at 23° C. The reaction mixture was subsequently poured into 500 ml of ice water. The mixture was stirred for a further 30 minutes and the solid that had formed was separated off, washed with water and then dried. Yield: 3.0 g (75%) of colorless crystals; mp.: 54-56° C.).

Workup

  1. temperaturewere heated
  2. stirringThe mixture was stirred for a further 30 minutes
  3. customthe solid that had formed
  4. customwas separated off
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-9b3119c35ff644f582f879b057b67380
Source dataset
uspto-grants-2002_01
Patent number
US06337305B1

Reaction notes

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