Methanethiol → Methyl 3-fluoro-2-(methylthio)benzoate

HRID 1491582Notes

Reaction equation

HRID 1491582 reaction equation
[CH3:1][SH:2].C(=O)([O-])[O-].[K+].[K+].F[C:10]1[C:19]([F:20])=[CH:18][CH:17]=[CH:16][C:11]=1[C:12]([O:14][CH3:15])=[O:13].[Cl-].[NH4+]>>[F:20][C:19]1[C:10]([S:2][CH3:1])=[C:11]([CH:16]=[CH:17][CH:18]=1)[C:12]([O:14][CH3:15])=[O:13]

Participants

5

Reactant 4

HCID 878MethanethiolHCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 2782927Methyl 2,3-difluorobenzoate

Product 1

HCID 18953297Methyl 3-fluoro-2-(methylthio)benzoateYield 70.8%

Conditions

Temperature
25 °C

Procedure

Approximately 12.6 g of methanethiol was dissolved in N,N-dimethylformide. Potassium carbonate (41.5 g) and methyl 2,3-difluorobenzoate (43.1 g) were added and the mixture stirred at 25° C. for 27 hours. Saturated ammonium chloride was added and the mixture partitioned between ether and water. The organic phase was washed with water, dried over magnesium sulphate, filtered and evaporated. The product was obtained by distillation to give 35.5 g of methyl 3-fluoro-2-methylsulphenylbenzoate, b.p. 140° C. (9mm Hg) as a clear oil. NMR (CDCl3) 2.5(3H, d), 3.9(3H,s), 7.2(1H,m), 7.3(1H,m), 7.5(1H, m).

Workup

  1. customthe mixture partitioned between ether and water
  2. washThe organic phase was washed with water
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. customevaporated
  6. customThe product was obtained by distillation

Sources & evidence

ORD record
ord-5b84e271d9694a8d978bf28bcbed9bae
Source dataset
uspto-grants-1994_12
Patent number
US05371064

Reaction notes

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