Ammonia → 4-BroMo-2,6-difluorobenzaMide, 96%

HRID 1366178Notes

Reaction equation

HRID 1366178 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]([F:11])[C:5]([C:6](O)=[O:7])=[C:4]([F:12])[CH:3]=1.O[N:14]1C2C=CC=CC=2N=N1.C(N=C=NCCCN(C)C)C.N>>[Br:1][C:2]1[CH:10]=[C:9]([F:11])[C:5]([C:6]([NH2:14])=[O:7])=[C:4]([F:12])[CH:3]=1

Participants

5

Reactant 4

HCID 222AmmoniaHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 27732984-Bromo-2,6-difluorobenzoic acid

Product 1

HCID 596566824-BroMo-2,6-difluorobenzaMide, 96%Yield 93%

Procedure

To a solution of 4-bromo-2,6-difluoro-benzoic acid (2.77 g, 11.7 mmol) and 1-hydroxybenzotriazole (1.74 g, 12.8 mmol) is added 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide (2.46 g, 12.9 mmol) and the solution is stirred at room temperature for 2 hours. After cooling at 0° C. is added aq. NH3 (1.74 mL) and the reaction mixture is stirred for an additional 20 hours. The solvent is evaporated in vacuo and the residue partitioned between diethyl ether and water. The aqueous phase is extracted several times with Et2O, the organic layers are then combined, washed with 1M HCl, sat. NaHCO3, dried over MgSO4, filtered and concentrated in vacuo to afford the benzamide as a white solid (2.56 g, 93%).

Workup

  1. temperatureAfter cooling at 0° C.
  2. stirringthe reaction mixture is stirred for an additional 20 hours
  3. customThe solvent is evaporated in vacuo
  4. customthe residue partitioned between diethyl ether and water
  5. extractionThe aqueous phase is extracted several times with Et2O
  6. washwashed with 1M HCl, sat. NaHCO3
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-02e2fb14293042ca9047fd3f1a22d56b
Source dataset
uspto-grants-2011_02
Patent number
US07893058B2

Reaction notes

Loading…