Formic Acid → Ethyl 2-[[3-(4-chlorophenyl)-1,2-benzisoxazol-6yl-]sulfinyl]-2-methylpropionate

HRID 745991Notes

Reaction equation

HRID 745991 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]3[CH:13]=[CH:14][C:15]([S:17][C:18]([CH3:25])([CH3:24])[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:16][C:11]=3[O:10][N:9]=2)=[CH:4][CH:3]=1.OO.C(O)=[O:29]>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]3[CH:13]=[CH:14][C:15]([S:17]([C:18]([CH3:24])([CH3:25])[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[O:29])=[CH:16][C:11]=3[O:10][N:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 284Formic AcidHCID 784Hydrogen Peroxide2×HCID 14097269HCID 14097269, compound

Product 1

HCID 13656095Ethyl 2-[[3-(4-chlorophenyl)-1,2-benzisoxazol-6yl-]sulfinyl]-2-methylpropionateYield 52%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3.0 g (8.0 mmole) of ethyl 2-[[3-(4-chlorophenyl)-1,2-benzisoxazol-6-yl]thio]-2-methylpropionate was combined in a flask with 0.91 g (1 eq.) of a 30% H2O2 solution, 10 ml of formic acid and 50 ml of dichloromethane. The mixture was briskly stirred and the reaction monitored by TLC. After 45 minutes, 1 ml more of a 30% H2O2 solution was added to consume the remaining starting material. The reaction was stopped when the TLC showed the starting material was consumed (at which point oxidation of the product to the sulfone will begin) and the reaction mixture was diluted with 3N HCl. The dichloromethane layer was separated, washed with 3N HCl, water, and a saturated salt solution, dried over sodium sulfate and evaporated to an oil. The oil was crystallized by adding methanol and the resulting solid was collected and recrystallized from methanol to yield 1.6 g (52%) of ethyl 2-[ [3-(4-chlorophenyl)-1,2-benzisoxazol-6yl-]sulfinyl]-2-methylpropionate, m.p. 89° C.

Workup

  1. customto consume the
  2. customwas consumed (at which point oxidation of the product to the sulfone
  3. additionwas diluted with 3N HCl
  4. customThe dichloromethane layer was separated
  5. washwashed with 3N HCl, water
  6. dry with materiala saturated salt solution, dried over sodium sulfate
  7. customevaporated to an oil
  8. customThe oil was crystallized
  9. additionby adding methanol
  10. customthe resulting solid was collected
  11. customrecrystallized from methanol

Sources & evidence

ORD record
ord-b2c8e43008c244c3ac3dfba5055fc917
Source dataset
uspto-grants-1986_07
Patent number
US04602028

Reaction notes

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