Methyl 4-(chloromethyl)benzoate → HCID 22672091, compound

HRID 1006553Notes

Reaction equation

HRID 1006553 reaction equation
[OH:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([C:11]([F:14])([F:13])[F:12])=[CH:4][N:3]=1.Cl[CH2:16][C:17]1[CH:26]=[CH:25][C:20]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][CH:18]=1>C1(C)C=CC=CC=1.[Ag]=O>[N+:8]([C:7]1[C:2]([O:1][CH2:16][C:17]2[CH:26]=[CH:25][C:20]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][CH:18]=2)=[N:3][CH:4]=[C:5]([C:11]([F:12])([F:14])[F:13])[CH:6]=1)([O-:10])=[O:9]

Participants

5

Reactant 2

HCID 36664Methyl 4-(chloromethyl)benzoateHCID 178526653HCID 178526653, compound

Product 1

HCID 22672091HCID 22672091, compoundYield 57.4%

Reagents, catalysts & solvents 2

HCID 92152Silver(II) oxideCatalystHCID 1140TolueneSolvent

Procedure

To a solution of 2-hydroxy-3-nitro-5-trifluoromethylpyridine (1.0 g) in toluene (10 ml), methyl 4-chloromethylbenzoate (1.32 g) and silver oxide (1.23 g) were added in a stream of argon. The mixture was refluxed for 18 hours with heating. The reaction mixture was filtered. The filtrate was concentrated. The residue was recrystallized from ethyl acetate to give the title compound (982 mg) having the following physical data.

Workup

  1. temperatureThe mixture was refluxed for 18 hours
  2. temperaturewith heating
  3. filtrationThe reaction mixture was filtered
  4. concentrationThe filtrate was concentrated
  5. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-ca5ec5f8de06474e91b4a1e23eefd8fd
Source dataset
uspto-grants-2004_09
Patent number
US06790866B2

Reaction notes

Loading…