Water → HCID 53676987, compound

HRID 341741Notes

Reaction equation

HRID 341741 reaction equation
[CH3:1][O-:2].[Na+].[Cl:4][C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[C:7](F)[C:6]=1[S:16][CH3:17].O>O1CCCC1>[Cl:4][C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[C:7]([O:2][CH3:1])[C:6]=1[S:16][CH3:17]

Participants

5

Reactant 3

HCID 962WaterHCID 10942334Sodium MethoxideHCID 53770449HCID 53770449, compound

Product 1

HCID 53676987HCID 53676987, compoundYield 84.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium methoxide (5.6 g) was added to a solution of methyl 4-chloro-2-fluoro-3-(methylsulphenyl)benzoate (85% pure, 19.2 g) in dry tetrahydrofuran and the mixture was stirred at room temperature overnight. Water was added and the mixture was extracted with ether, dried (MgSO4) and filtered. The filtrate was evaporated to dryness to give methyl 4-chloro-2-methoxy-3-(methylsulphenyl)benzoate (17.1 g) as a yellow oil NMR (CDCl3) 2.5(s,3H), 3.95(s,3H), 4.0(s,3H), 7.25(d,1H), 7.65(d, 1H) contaminated with 15% methyl 4-chloro-3-(chloromethylsulphenyl)-2-methoxybenzoate (determined by the ratio of NMR signals).

Workup

  1. extractionthe mixture was extracted with ether
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-666413c7dacf4d2cadcb8aad95fc9919
Source dataset
uspto-grants-1999_01
Patent number
US05856274

Reaction notes

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