Hydrochloric Acid → HCID 57701115, compound

HRID 332571

Reaction equation

HRID 332571 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[C:3]=1[OH:10].I[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=1.C([O-])([O-])=O.[Cs+].[Cs+].CN(C)CC(O)=O.Cl>O1CCOCC1.[Cu]I>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[C:3]=1[O:10][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 673N,N-DimethylglycineHCID 10796Cesium carbonateHCID 125741-Iodo-3-nitrobenzeneHCID 27373672-Fluoro-6-methoxyphenol

Product 1

HCID 57701115HCID 57701115, compoundYield 78.7%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
98 °C

Procedure

To a 250 mL pressure resistant vial which contained a mixture of 2-fluoro-6-methoxy-phenol (1000 mg, 7 mmole), 1-iodo-3-nitro-benzene (2500 mg, 10 mmole), Cs2CO3 (1200 mg, 7 mmole) and N,N-dimethylglycine.HCl (200 mg, 1.5 mmole) in dioxane (40 mL) was added CuI (140 mg, 0.7 mmole) at rt. The reaction mixture was bumbled with Ar for 5 min at rt and then the vial was sealed. The reaction mixture was stirred and heated to 98° C. for 5 d. After cooling to rt, the reaction mixture was poured into 250 mL ice-water which was extracted with ethyl acetate (3×50 mL), washed with water (2×50 mL), brine (50 mL) and dried over Na2SO4. After removal of solvent, the residue was purified by silica gel column chromatography with ethyl acetate/hexane as eluent to give 1450 mg (75% yield) of product (10).

Workup

  1. customthe vial was sealed
  2. temperatureAfter cooling to rt
  3. extractionwas extracted with ethyl acetate (3×50 mL)
  4. washwashed with water (2×50 mL), brine (50 mL)
  5. dry with materialdried over Na2SO4
  6. customAfter removal of solvent
  7. customthe residue was purified by silica gel column chromatography with ethyl acetate/hexane as eluent

Sources & evidence

ORD record
ord-7d5582b738464520abf25e5d6d00ca9e
Source dataset
uspto-grants-2014_11
Patent number
US08877816B2

Linked notes

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