Thionyl Chloride → Chloro-(4-methylsulfanyl-phenyl)-acetic acid ethyl ester

HRID 857283Notes

Reaction equation

HRID 857283 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[CH:5](O)[C:6]1[CH:11]=[CH:10][C:9]([S:12][CH3:13])=[CH:8][CH:7]=1)[CH3:2].O=S(Cl)[Cl:18]>C(Cl)Cl.[NH4+].[Cl-]>[CH2:1]([O:3][C:4](=[O:15])[CH:5]([Cl:18])[C:6]1[CH:11]=[CH:10][C:9]([S:12][CH3:13])=[CH:8][CH:7]=1)[CH3:2]

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 20814961Hydroxy-(4-methylsulfanyl-phenyl)-acetic acid ethyl ester

Product 1

HCID 62226237Chloro-(4-methylsulfanyl-phenyl)-acetic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 25517Ammonium ChlorideSolvent

Procedure

To a solution of the hydroxy-(4-methylsulfanyl-phenyl)-acetic acid ethyl ester of Step 2 (1.0 eq) in CH2Cl2 (0.2M) was added SOCl2 (5 eq). The resulting mixture was stirred at room temperature for 12 h, poured in saturated aqueous NH4Cl and extracted with Et2O (2×). The combined organic extracts were washed with brine, dried over MgSO4, filtered and concentrated. Flash chromatography (Hex:EtOAc; 9.5:0.5) afforded the desired compound as a yellow solid.

Workup

  1. extractionextracted with Et2O (2×)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c65b32086aae4f4e89be96f91deca31a
Source dataset
uspto-grants-2006_12
Patent number
US07144896B2

Reaction notes

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