Bromine → 2(4-Dibromomethylphenyl)pyridine

HRID 1387683Notes

Reaction equation

HRID 1387683 reaction equation
C1(C)C=CC(C2C=CC=CN=2)=CC=1.[Br:14]Br.[Br:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=2)=[CH:20][CH:19]=1>ClC1C=CC=CC=1>[Br:16][CH:17]([Br:14])[C:18]1[CH:19]=[CH:20][C:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=2)=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 782192-(p-Tolyl)pyridineHCID 98875912-(4-(Bromomethyl)phenyl)pyridine

Product 1

HCID 98266562(4-Dibromomethylphenyl)pyridineYield 60.7%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Conditions

Temperature
115 °C

Procedure

In a 100 ml four neck flask were placed 2-(4-tolyl)pyridine (5.0 g, 29.6 mmol) and chlorobenzene (18 ml), and bromine (9.4 g, 59.1 mmol) was added dropwise while heating the mixture at 110-120 ° C. over 12 hours. The reaction mixture was stirred with heating at a temperature in the above-mentioned range for 1 hour and analyzed by HPLC. As a result, 2-(4-bromomethylphenyl)pyridine was confirmed to have been produced in a 60.7% yield. The obtained reaction mixture was cooled and the precipitated 2-(4-bromomethylphenyl)pyridine salt was collected by filtration. The filtrate was neutralized with 5% aqueous sodium hydroxide solution. After washing with water, the mixture was dried over anhydrous magnesium sulfate. Chlorobenzene was evaporated under reduced pressure and the residue was subjected to silica gel column chromatography (eluent: ethyl acetate-hexane) to give 2-(4-dibromomethylphenyl)pyridine in a 1.2 g yield. From the 1H-NMR analysis, the product was found to be 2-(4-dibromomethylphenyl)pyridine. 2-(4-dibromomethylphenyl)pyridine 1H-NMR(CDCl3, ppm) δ: 6.70(s,1H), 7.23-7.29(m,1H), 7.66-7.68(d,2H), 7.68-7.78(m,2H), 7.98-8.01(d,2H), 8.69-8.71(m,1H)

Workup

  1. additionwas added dropwise
  2. temperaturewith heating at a temperature in the above-mentioned range for 1 hour
  3. customto have been produced in a 60.7% yield
  4. customThe obtained reaction mixture
  5. temperaturewas cooled
  6. filtrationthe precipitated 2-(4-bromomethylphenyl)pyridine salt was collected by filtration
  7. washAfter washing with water
  8. dry with materialthe mixture was dried over anhydrous magnesium sulfate
  9. customChlorobenzene was evaporated under reduced pressure

Sources & evidence

ORD record
ord-3e866caeaaf143d4ac7239367846b3bb
Source dataset
uspto-grants-2001_07
Patent number
US06268503B1

Reaction notes

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