Methanol → HCID 59347928, compound

HRID 20828Notes

Reaction equation

HRID 20828 reaction equation
[CH3:1][S:2][C:3]1[CH:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:9]=[C:8]([C:16]([F:19])([F:18])[F:17])[C:4]=1[C:5](O)=[O:6].C(Cl)(=O)C([Cl:23])=O.CO>C(Cl)Cl.CN(C=O)C>[CH3:1][S:2][C:3]1[CH:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:9]=[C:8]([C:16]([F:19])([F:18])[F:17])[C:4]=1[C:5]([Cl:23])=[O:6]

Participants

6

Reactant 3

HCID 887MethanolHCID 65578Oxalyl chlorideHCID 593478222-Methylthio-4,6-bis(trifluoromethyl)benzoic acid

Product 1

HCID 59347928HCID 59347928, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of the mixture containing 2-(methylthio)-4,6-bis(trifluoromethyl)benzoic acid D54 (225 mg) in dry DCM (4 ml), containing dry DMF (1drop), was treated with oxalyl chloride (87 ul, 1.0 mmol) and stirred at room temperature for 1 hour. The solvent was removed under reduced pressure to afford a crude product which was treated with dry methanol (2 ml) and stirred at room temperature overnight. The solvent was then carefully removed under reduced pressure. The residue was chromatographed on silica gel, eluting with 0-10% ethyl acetate in pentane to afford the title product 2-(methylthio)-4,6-bis(trifluoromethyl)benzoyl chloride (60 mg). 1H NMR (CDCl3) δ: 2.62 (3H, s), 7.77 (1H, s), 7.82 (1H, s). Further elution gave methyl 2,4-bis(trifluoromethyl)benzoate (100 mg).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customto afford a crude product which
  3. stirringstirred at room temperature overnight
  4. customThe solvent was then carefully removed under reduced pressure
  5. customThe residue was chromatographed on silica gel
  6. washeluting with 0-10% ethyl acetate in pentane

Sources & evidence

ORD record
ord-6248bb21322f499096a72edebf593f54
Source dataset
uspto-grants-2010_06
Patent number
US07745642B2

Reaction notes

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