Triethylamine → HCID 68600944, compound

HRID 448946Notes

Reaction equation

HRID 448946 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[NH:5][CH3:6].C(N(CC)CC)C.[Br:18][C:19]1[C:20]([Cl:29])=[CH:21][C:22]([F:28])=[C:23]([CH:27]=1)[C:24](Cl)=[O:25]>C(Cl)Cl>[Br:18][C:19]1[C:20]([Cl:29])=[CH:21][C:22]([F:28])=[C:23]([CH:27]=1)[C:24]([N:5]([C:4]1[CH:7]=[CH:8][CH:9]=[CH:10][C:3]=1[O:2][CH3:1])[CH3:6])=[O:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27595792-Methoxy-N-methylanilineHCID 86642580HCID 86642580, compound

Product 1

HCID 68600944HCID 68600944, compoundYield 77.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Methoxy-N-methylaniline (7.4 g, 53.8 mmol) and triethylamine (10.9 g, 107.7 mmol) were added to 5-bromo-4-chloro-2-fluoro-benzoyl chloride (Step 21D, 11.7 g, 43.1 mmol) in DCM (200 mL) at 0° C. The mixture was then allowed to warm to rt and concentrated. The mixture was partitioned in water and ethyl acetate. The organic layer was separated, washed with NaHSO4 solution, water and brine, and was dried. After filtration and concentration, the residue was purified via silica gel flash column chromatography eluting with ethyl acetate in hexane (50%) to give 5-bromo-4-chloro-2-fluoro-N-(2-methoxy-phenyl)-N-methyl-benzamide (12.5 g). MS: [M+H]+374.0/372.0; tR=2.70 min (method 1)

Workup

  1. concentrationconcentrated
  2. customThe mixture was partitioned in water
  3. customThe organic layer was separated
  4. washwashed with NaHSO4 solution, water and brine
  5. customwas dried
  6. filtrationAfter filtration and concentration
  7. customthe residue was purified via silica gel flash column chromatography
  8. washeluting with ethyl acetate in hexane (50%)

Sources & evidence

ORD record
ord-9b4f459f23754e318f6ac2b85e20347e
Source dataset
uspto-grants-2013_07
Patent number
US08481738B2

Reaction notes

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