Ethanol → 5-({[2-Bromo-4-fluoro-5-(methyloxy)phenyl]amino}methylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione

HRID 639012Notes

Reaction equation

HRID 639012 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:3]=1[NH:4]OC.[CH3:12][C:13]1([CH3:21])[O:18][C:17](=[O:19])[CH2:16][C:15](=[O:20])[O:14]1.[CH3:22][O:23]C(OC)OC.[CH2:29](O)C>>[Br:1][C:2]1[CH:10]=[C:9]([F:11])[C:8]([O:23][CH3:22])=[CH:7][C:3]=1[NH:4][CH:29]=[C:16]1[C:17](=[O:19])[O:18][C:13]([CH3:21])([CH3:12])[O:14][C:15]1=[O:20]

Participants

5

Reactant 4

HCID 702EthanolHCID 9005Trimethyl orthoformateHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 866167832-Bromo-4-fluoro-(methyloxy)aniline

Product 1

HCID 179763135-({[2-Bromo-4-fluoro-5-(methyloxy)phenyl]amino}methylidene)-2,2-dimethyl-1,3-dioxane-4,6-dioneYield 92%

Procedure

A mixture of 2-bromo-4-fluoro-(methyloxy)aniline (15 g, 68 mmol), 2,2-dimethyl-[1,3]dioxane-4,6-dione (11.8 g, 82 mmol) and trimethylorthoformate (13.6 mL) in ethanol (70 mL) was refluxed for 3 hours. After cooling, the solid was filtered off, washed with ethanol and air dried. To give the product (23.3 g, 92%) as a white solid. LC-MS (ES) (M+H)+ m/z=374.

Workup

  1. temperaturewas refluxed for 3 hours
  2. temperatureAfter cooling
  3. filtrationthe solid was filtered off
  4. washwashed with ethanol and air
  5. customdried

Sources & evidence

ORD record
ord-20a6ab15ce604288ab261ba0e88cb483
Source dataset
uspto-grants-2010_04
Patent number
US07691850B2

Reaction notes

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