Pyridine → 4-Nitrobenzyl bromoacetate

HRID 1632745Notes

Reaction equation

HRID 1632745 reaction equation
[Br:1][CH2:2][C:3](Cl)=[O:4].[N+:6]([C:9]1[CH:16]=[CH:15][C:12]([CH2:13][OH:14])=[CH:11][CH:10]=1)([O-:8])=[O:7].N1C=CC=CC=1>O1CCCC1>[Br:1][CH2:2][C:3]([O:14][CH2:13][C:12]1[CH:11]=[CH:10][C:9]([N+:6]([O-:8])=[O:7])=[CH:16][CH:15]=1)=[O:4]

Participants

5

Reactant 3

HCID 1049PyridineHCID 692754-Nitrobenzyl alcoholHCID 89602Bromoacetyl chloride

Product 1

HCID 70153214-Nitrobenzyl bromoacetateYield 40.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Bromoacetyl chloride (113 g) was dropwise added to a stirred solution of 4-nitrobenzyl alcohol (9.2 g) and pyridine (10 ml) in dry tetrahydrofuran (100 ml) at 0° C. over 50 minutes. The mixture was stirred at 0° to 5° C. for 30 minutes, and evaporated in vacuo. The residue was dissolved in a mixture of chloroform (70 ml) and water (20 ml), and then the organic layer was separated. The organic layer was washed with a diluted aqueous hydrochloric acid and water in turn, and then dried over anhydrous magnesium sulfate. The solution was evaporated in vacuo, and the residue was recrystallized from methanol to give crystals (6.74 g) of 4-nitrobenzyl bromoacetate.

Workup

  1. customevaporated in vacuo
  2. dissolutionThe residue was dissolved in a mixture of chloroform (70 ml) and water (20 ml)
  3. customthe organic layer was separated
  4. washThe organic layer was washed with a diluted aqueous hydrochloric acid and water in turn
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solution was evaporated in vacuo
  7. customthe residue was recrystallized from methanol

Sources & evidence

ORD record
ord-638dfccceb9e41d4af06e09c0e6d5c90
Source dataset
uspto-grants-1984_10
Patent number
US04477447

Reaction notes

Loading…