Hydrochloric Acid → HCID 54204871, compound

HRID 2256961Notes

Reaction equation

HRID 2256961 reaction equation
[CH3:1][S-:2].[Na+].F[C:5]1[C:14]([C:15]([O:17][CH3:18])=[O:16])=[C:13]([C:19]([F:22])([F:21])[F:20])[CH:12]=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8].O.[OH-].[Li+].Cl>C1(C)C(C)=CC=CC=1>[CH3:18][O:17][C:15]([C:14]1[C:5]([S:2][CH3:1])=[C:6]([CH:11]=[CH:12][C:13]=1[C:19]([F:22])([F:21])[F:20])[C:7]([O:9][CH3:10])=[O:8])=[O:16]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 4378561Sodium methanethiolateHCID 54388633HCID 54388633, compound

Product 1

HCID 54204871HCID 54204871, compoundYield 50.1%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

Sodium thiomethoxide (6.83 g) was added to a solution of methyl 2-fluoro-3-methoxycarbonyl-4-trifluoromethylbenzoate (24.85 g) in xylene. After stirring for 0.5 hours lithium hydroxide monohydrate (4.10 g) was added and the mixture was stirred for 48 hours. Hydrochloric acid (2M) was added. It was extracted with ether, washed with water, dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was triturated with cyclohexane. The solid was filtered off and the filtrate was evaporated to dryness to give methyl 3-methoxycarbonyl-2-(methylsulphenyl)-4-trifluoromethylbenzoate (13.71 g) as a yellow oil NMR (CDCl3) 2.4(s,3H), 3.95 (s,6H), 7.65 (s,2H).

Workup

  1. additionwas added
  2. extractionIt was extracted with ether
  3. washwashed with water
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customThe filtrate was evaporated to dryness
  7. customthe residue was triturated with cyclohexane
  8. filtrationThe solid was filtered off
  9. customthe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-2979b34192ec422f805d227e303cf1a9
Source dataset
uspto-grants-1997_08
Patent number
US05656573

Reaction notes

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