Pyridine → 2-Bromoethyl 4-nitrobenzoate

HRID 1369296Notes

Reaction equation

HRID 1369296 reaction equation
[Br:1][CH:2](O)[CH3:3].N1C=CC=CC=1.[N+:11]([C:14]1[CH:22]=[CH:21][C:17]([C:18](Cl)=[O:19])=[CH:16][CH:15]=1)([O-:13])=[O:12].CC[O:25]CC>>[Br:1][CH2:2][CH2:3][O:19][C:18](=[O:25])[C:17]1[CH:21]=[CH:22][C:14]([N+:11]([O-:13])=[O:12])=[CH:15][CH:16]=1

Participants

5

Reactant 4

HCID 1049PyridineHCID 3283Diethyl Ether3×HCID 85024-Nitrobenzoyl chlorideHCID 14202443Ethanol, 1-bromo-

Product 1

HCID 2803962-Bromoethyl 4-nitrobenzoate

Procedure

Under a nitrogen atmosphere, bromoethanol (29 mmols) was dissolved in 25 mL ether. Pyridine (34 mmols) was added to the solution, followed by a solution of 4-nitrobenzoyl chloride (27 mmols) in 35 mL ether. The reaction was stirred overnight, and a white precipitate was formed. Ether (50 mL) was added, and the reaction mixture was then washed with aqueous KHSO4, aqueous NaHCO3, and water. The ether layer was then dried over Na2SO4, filtered, and concentrated to give 6.3 g of 4-nitrobenzoic acid 2-bromo-ethyl ester. Material was used in coupling reactions without further purification.

Workup

  1. customa white precipitate was formed
  2. washthe reaction mixture was then washed with aqueous KHSO4, aqueous NaHCO3, and water
  3. dry with materialThe ether layer was then dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ec6f01b7154740df8b9007512e9365bb
Source dataset
uspto-grants-2003_06
Patent number
US06576791B1

Reaction notes

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