Pyridine → 2-Bromoethyl 4-nitrobenzoate

HRID 990626Notes

Reaction equation

HRID 990626 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-86e4749013e74bd8bcc013ba36b1f18d
Source dataset
uspto-grants-2002_10
Patent number
US06462034B1

Reaction notes

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