Water → HCID 89443721, compound

HRID 1771828Notes

Reaction equation

HRID 1771828 reaction equation
[F:1][C:2]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=2)=[CH:10][C:3]=1[C:4](N(OC)C)=[O:5].[CH3:21][Mg+].[Br-].O>C1COCC1>[F:1][C:2]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=2)=[CH:10][C:3]=1[C:4](=[O:5])[CH3:21]

Participants

5

Reactant 3

HCID 962WaterHCID 89445230HCID 89445230, compoundHCID 178418689HCID 178418689, compound

Product 1

HCID 89443721HCID 89443721, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-fluoro-5-(3-fluorophenyl)-N-methoxy-N-methyl-benzamide (1.8 g, 6.5 mmol, 1.0 eq) in THF (14 mL) at −20° C. was added MeMgBr (3.2 mL, 9.7 mmol, 1.5 eq). The mixture was stirred at 0° C. for 2 h then water was added and the aqueous layer was extracted with EtOAc. The combined organic extracts were washed with brine, dried (Na2SO4), filtered and evaporated in vacuo. The residue obtained was purified by column chromatography (petroleum ether: EtOAc, 20:1 to 10:1) to give the title compound as a white solid (1.3 g, 86%).

Workup

  1. extractionthe aqueous layer was extracted with EtOAc
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe residue obtained
  7. customwas purified by column chromatography (petroleum ether: EtOAc, 20:1 to 10:1)

Sources & evidence

ORD record
ord-848cf7ed24904ca8bf4971349a8553f1
Source dataset
uspto-grants-2016_02
Patent number
US09249085B2

Reaction notes

Loading…