Dimethylformamide → HCID 71270695, compound

HRID 1502022Notes

Reaction equation

HRID 1502022 reaction equation
C(Cl)(=O)C(Cl)=O.[Br:7][C:8]1[C:9]([O:18][CH3:19])=[C:10]([C:14]([F:17])=[CH:15][CH:16]=1)[C:11](O)=[O:12].C[N:21](C=O)C>C(Cl)Cl>[Br:7][C:8]1[C:9]([O:18][CH3:19])=[C:10]([C:14]([F:17])=[CH:15][CH:16]=1)[C:11]([NH2:21])=[O:12]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 712707193-BROMO-6-FLUORO-2-METHOXYBENZOIC ACID

Product 1

HCID 71270695HCID 71270695, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

Oxalyl chloride (15 mL) was added dropwise at 0° C. to a suspension of 3-bromo-6-fluoro-2-methoxybenzoic acid (15 g, 60 mmol) in 100 mL of DCM with 0.5 mL of DMF. The mixture was stirred at 25° C. for 2 hours and the clear solution was concentrated to dryness under reduced pressure. The residue dissolved in 60 mL of anhydrous acetonitrile was added to 600 mL of aqueous NH3.H2O at 0° C. and stirred for 2 hours, then filtered to give 3-bromo-6-fluoro-2-methoxybenzamide.

Workup

  1. concentrationthe clear solution was concentrated to dryness under reduced pressure
  2. dissolutionThe residue dissolved in 60 mL of anhydrous acetonitrile
  3. additionwas added to 600 mL of aqueous NH3.H2O at 0° C.
  4. stirringstirred for 2 hours
  5. filtrationfiltered

Sources & evidence

ORD record
ord-90e90e361e3645bdaea688565dd5da50
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

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