Sodium Sulfite → HCID 18620115, compound

HRID 1862615Notes

Reaction equation

HRID 1862615 reaction equation
[Br:1][CH2:2][CH2:3][C:4]1[CH:16]=[CH:15][C:7]([O:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:6][C:5]=1[O:17][CH3:18].[Cl:19]OC(C)(C)C.S([O-])([O-])=O.[Na+].[Na+]>ClCCl.O>[Br:1][CH2:2][CH2:3][C:4]1[C:5]([O:17][CH3:18])=[CH:6][C:7]([O:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:15]([Cl:19])[CH:16]=1

Participants

6

Reactant 3

HCID 24437Sodium SulfiteHCID 521297Tert-Butyl hypochloriteHCID 18620082HCID 18620082, compound

Product 1

HCID 18620115HCID 18620115, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of ethyl 2-[4-(2-bromoethyl)-3-methoxyphenoxy]acetate (640 mg) in dichloromethane (4 ml) was added tert-butyl hypochlorite (251 μl) at room temperature, and the mixture was stirred for 30 minutes. To the reaction mixture was added a solution of sodium sulfite (504 mg) in water (2 ml) and the resulting mixture was stirred for 30 minutes at room temperature. The mixture was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. After the solvent was removed under reduced pressure, purification of the residue by medium pressure liquid column chromatography on silica gel (eluent: hexane/ethyl acetate=7/1) gave ethyl 2-[4-(2-bromoethyl)-2-chloro-5-methoxyphenoxy]acetate (685 mg).

Workup

  1. stirringthe resulting mixture was stirred for 30 minutes at room temperature
  2. extractionThe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customAfter the solvent was removed under reduced pressure, purification of the residue by medium pressure liquid column chromatography on silica gel (eluent: hexane/ethyl acetate=7/1)

Sources & evidence

ORD record
ord-5e46c0bcbf144618a441d3025af3b47c
Source dataset
uspto-grants-2003_03
Patent number
US06538152B1

Reaction notes

Loading…