Methanol → HCID 58452437, compound

HRID 70575Notes

Reaction equation

HRID 70575 reaction equation
[H-].C[O:3]CCO[Al+]OCCOC.[Na+].[H-].[Br:15][C:16]1[CH:21]=[CH:20][C:19]([S:22][CH:23]2[CH2:25][CH2:24]2)=[C:18]([Cl:26])[CH:17]=1.CO.[OH2:29]>O1CCCC1>[Br:15][C:16]1[CH:21]=[CH:20][C:19]([S:22]([CH:23]2[CH2:24][CH2:25]2)(=[O:3])=[O:29])=[C:18]([Cl:26])[CH:17]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962Water2×HCID 21584525Sodium bis(2-methoxyethoxy)aluminiumhydride2×HCID 58452584HCID 58452584, compound

Product 1

HCID 58452437HCID 58452437, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Oxone(R) (20.3 g) was added to a solution of 4-bromo-2-chloro-1-(cyclopropylsulfanyl)benzene obtained in Reference Example 5-22 (964 mg) in tetrahydrofuran (20 mL)-methanol (20 mL)-water (10 mL), and the mixture was stirred at room temperature for one day. Oxone(R) (6.8 g) was further added and the mixture was stirred at room temperature for 18 hours. Water was added to the reaction solution, followed by extraction with chloroform. The organic layer was dried over anhydrous magnesium sulfate and filtered. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform only) to give the title compound as a pale yellow amorphous (597 mg, 55%).

Workup

  1. stirringthe mixture was stirred at room temperature for 18 hours
  2. extractionfollowed by extraction with chloroform
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customThe solvent was then evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (chloroform only)

Sources & evidence

ORD record
ord-8bcaa7ff2ea546a39b6e4c98f3640ab5
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Reaction notes

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