N-bromobutanimide → 5-Bromo-4-(trifluoromethyl)pyridin-2-amine

HRID 63784Notes

Reaction equation

HRID 63784 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][N:3]=1.[Br:12]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[NH2:1][C:2]1[CH:7]=[C:6]([C:8]([F:9])([F:11])[F:10])[C:5]([Br:12])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 27783152-Amino-4-(trifluoromethyl)pyridine

Product 1

HCID 288753485-Bromo-4-(trifluoromethyl)pyridin-2-amineYield 58.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2-amino-4-trifluoromethylpyridine (5 g, 30.8 mmol, Langfang Beixin Chemical Co., Hebei) was dissolved in 100 mL of chloroform and N-bromosuccinimide (5.92 g, 33.3 mmol) was added in batches. The mixture was stirred in darkness or away from light at room temperature for 3 hours. The reaction mixture was concentrated and purified by column chromatography with gradient elution (petroleum ether: ethyl acetate=10:1 and dichloromethane), so as to give 4.33 g of red solid. Yield: 58.2%. LC-MS: 240 (M+1), 242 (M+2+1).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by column chromatography with gradient elution (petroleum ether: ethyl acetate=10:1 and dichloromethane)

Sources & evidence

ORD record
ord-247f5cd8103c45698d5245051deb6a86
Source dataset
uspto-grants-2016_09
Patent number
US09447101B2

Reaction notes

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