Citric Acid → Bromo-acetic acid 2,4-dinitro-phenyl ester

HRID 1959571Notes

Reaction equation

HRID 1959571 reaction equation
[Br:1][CH2:2][C:3](Br)=[O:4].[N+:6]([C:9]1[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:11][C:10]=1[OH:18])([O-:8])=[O:7].N1C=CC=CC=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(Cl)Cl>[N+:6]([C:9]1[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:11][C:10]=1[O:18][C:3](=[O:4])[CH2:2][Br:1])([O-:8])=[O:7]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 1049PyridineHCID 14932,4-DinitrophenolHCID 61147Bromoacetyl bromide

Product 1

HCID 11278141Bromo-acetic acid 2,4-dinitro-phenyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Under argon atmosphere bromo-acetyl bromide (2.67 mL, 30.66 mmol) dissolved in DCM (15 mL) was added within 15 min to a mixture of 2,4-dinitro-phenol (5.13 g, 27.88 mmol) and pyridine (2.92 mL, 36.24 mmol) in DCM (40 mL) at 0° C. After 1 h at RT, aqueous citric acid solution (10%, 30 mL) was added to the reaction mixture. The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo. The resulting residue recrystallized from diethyl ether (75 mL) to afford the title compound.

Workup

  1. dry with materialThe organic layer was dried over Na2SO4
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo
  4. customThe resulting residue recrystallized from diethyl ether (75 mL)

Sources & evidence

ORD record
ord-73231533228d4ba39352ee3bca1e76e9
Source dataset
uspto-grants-2013_04
Patent number
US08410134B2

Reaction notes

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