Hydrochloric Acid → 5-bromo-2-fluoro-N-methoxy-N-methylbenzamide

HRID 1864761Notes

Reaction equation

HRID 1864761 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:11])=[C:6]([CH:10]=1)[C:7](O)=[O:8].C(Cl)(=O)C(Cl)=O.Cl.[CH3:19][NH:20][O:21][CH3:22].C(N(CC)CC)C.Cl>C(Cl)Cl.CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:11])=[C:6]([CH:10]=1)[C:7]([N:20]([O:21][CH3:22])[CH3:19])=[O:8]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27363155-Bromo-2-fluorobenzoic acid

Product 1

HCID 606295205-bromo-2-fluoro-N-methoxy-N-methylbenzamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 20.0 g (91.3 mmol) 5-bromo-2-fluorobenzoic acid in 1 L CH2Cl2 was added 12.0 mL (137 mmol) oxalyl chloride and 3 drops of DMF. After stirring for 6 h, the reaction was concentrated by rotary evaporation, the residue was dissolved in 1 L of CH2Cl2, 11.6 g (119 mmol) N,O-dimethylhydroxylamine hydrochloride and 63.6 mL (456 mmol) triethylamine were added and the reaction was stirred overnight. The reaction was dumped into a separatory funnel with 1 M HCl, the layers were separated, the organic was washed with 1M NaOH, then water, dried over Na2SO4 and concentrated to provide 3-1 as a colorless oil. Data for 3-1: LC/MS: rt=1.76 min; m/z=262 (M+1).

Workup

  1. concentrationthe reaction was concentrated by rotary evaporation
  2. dissolutionthe residue was dissolved in 1 L of CH2Cl2
  3. stirringthe reaction was stirred overnight
  4. customthe layers were separated
  5. washthe organic was washed with 1M NaOH
  6. dry with materialwater, dried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-20be464547d24aa6bbd745012d0e1359
Source dataset
uspto-grants-2009_12
Patent number
US07625936B2

Reaction notes

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