Triethylamine → Methyl 2-chloro-2-(2-fluoro-4,5-dimethoxyphenyl)acetate

HRID 1667596Notes

Reaction equation

HRID 1667596 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([O:10][CH3:11])=[CH:4][C:3]=1[CH:12](O)[C:13]([O:15][CH3:16])=[O:14].C(N(CC)CC)C.S([Cl:29])(C)(=O)=O>C(Cl)Cl>[Cl:29][CH:12]([C:3]1[CH:4]=[C:5]([O:10][CH3:11])[C:6]([O:8][CH3:9])=[CH:7][C:2]=1[F:1])[C:13]([O:15][CH3:16])=[O:14]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 57448188Methyl 2-(2-fluoro-4,5-dimethoxyphenyl)-2-hydroxyacetate

Product 1

HCID 57448189Methyl 2-chloro-2-(2-fluoro-4,5-dimethoxyphenyl)acetateYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 7A (280 mg, 1.2 mmol) in CH2Cl2 (5 mL) at 0° C. was added triethylamine (0.42 mL, 3.0 mmol) followed by mesyl chloride (0.12 mL, 1.5 mmol). After stirring at rt overnight, the reaction was filtered, concentrated and purified via silica gel chromatography (0-30% ethyl acetate/hexanes) to provide 7B (268 mg, 89%).

Workup

  1. filtrationthe reaction was filtered
  2. concentrationconcentrated
  3. custompurified via silica gel chromatography (0-30% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-db2382aa09d64da395f4f001bfb2adf5
Source dataset
uspto-grants-2011_10
Patent number
US08044242B2

Reaction notes

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