Toluene → Ethyl 3-chloro-2-fluoropropionate

HRID 1468222Notes

Reaction equation

HRID 1468222 reaction equation
S(Cl)([Cl:3])=O.O[CH2:6][CH:7]([F:13])[C:8]([O:10][CH2:11][CH3:12])=[O:9].C1(C)C=CC=CC=1>N1C=CC=CC=1>[Cl:3][CH2:6][CH:7]([F:13])[C:8]([O:10][CH2:11][CH3:12])=[O:9]

Participants

5

Reactant 3

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 13572114Ethyl 2-fluoro-3-hydroxypropanoate

Product 1

HCID 12865311Ethyl 3-chloro-2-fluoropropionate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

An amount of thionyl chloride of 8.99 g (0.08 mol) was introduced at 20-25° C. into a dry 50 ml round-bottomed flask under a nitrogen atmosphere. Ethyl 3-hydroxy-2-fluoropropionate (10.0 g, 0.07 mol) were subsequently metered in in 1 h and the mixture was subsequently stirred at ambient temperature for a further 2 h. An amount of toluene of 3.98 g (0.04 mol), together with 0.286 g of pyridine (5 mol %), were introduced into a second round-bottomed flask with an Anschutz head and the mixture was heated to 80° C., The mixture from the 1st round-bottomed flask was added dropwise to the preheated solution in 1 h at 75-85° C. Solvents were distilled off under reduced pressure and the residue was subsequently finely distilled at 120° C. and 10 mbar. 4.1 g of distillate were obtained as a colorless liquid.

Workup

  1. customwere subsequently metered in in 1 h
  2. temperaturethe mixture was heated to 80° C.
  3. additionThe mixture from the 1st round-bottomed flask was added dropwise to the preheated solution in 1 h at 75-85° C
  4. distillationSolvents were distilled off under reduced pressure
  5. distillationthe residue was subsequently finely distilled at 120° C.
  6. custom4.1 g of distillate were obtained as a colorless liquid

Sources & evidence

ORD record
ord-c5fcb319967e4acca688455f32585fdf
Source dataset
uspto-grants-2015_04
Patent number
US09000210B2

Reaction notes

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