Dimethylformamide → 3-Bromo-5-chlorobenzamide

HRID 657361Notes

Reaction equation

HRID 657361 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([Cl:11])[CH:10]=1)[C:5](O)=[O:6].C(Cl)(=O)C(Cl)=O.C[N:19](C=O)C.[OH-].[NH4+]>C(Cl)Cl.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([Cl:11])[CH:10]=1)[C:5]([NH2:19])=[O:6]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 14923Ammonium HydroxideHCID 331283-Bromo-5-chlorobenzoic acidHCID 65578Oxalyl chloride

Product 1

HCID 534174713-Bromo-5-chlorobenzamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-Bromo-5-chlorobenzoic acid (2.35 g, 10 mmol) was suspended in CH2Cl2 (50 mL) and stirred under argon at room temperature. Oxalyl chloride (2.53 g, 20 mmol) was added followed by DMF (10 μL), and the mixture stirred overnight. The solvents were pumped off. The residue was taken up in EtOAc and added to concentrated ammonium hydroxide (10 mL). This was stirred for thirty mins. The phases were separated and the organic phase washed 1× with brine, dried over anhydrous Na2SO4, filtered, and evaporated. The residue was crystallized from EtOAc/hexane to give the title compound as a white crystalline solid. LC-MS m/z 233.7 (M+H)+, 1.57 min (ret time); analytical HPLC shows 96.5% purity, (ret time: 12.131 min).

Workup

  1. stirringthe mixture stirred overnight
  2. stirringThis was stirred for thirty mins
  3. customThe phases were separated
  4. washthe organic phase washed 1× with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was crystallized from EtOAc/hexane

Sources & evidence

ORD record
ord-067ddb68200f4cd98a3ccde2686400f7
Source dataset
uspto-grants-2011_12
Patent number
US08071588B2

Reaction notes

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