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

HRID 1438181Notes

Reaction equation

HRID 1438181 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 139A (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 139B (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-3da6bb0fa6c04fc6bfa2205279827696
Source dataset
uspto-grants-2009_11
Patent number
US07622585B2

Reaction notes

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