2-Chloropropionyl chloride → 4-Chloro-1-phenylpentan-3-one

HRID 548001Notes

Reaction equation

HRID 548001 reaction equation
[Cl:1][CH:2]([CH3:6])[C:3](Cl)=[O:4].[CH2:7]([Mg]Br)[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>O1CCCC1>[Cl:1][CH:2]([CH3:6])[C:3](=[O:4])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 1110192-Chloropropionyl chlorideHCID 178419670HCID 178419670, compound

Product 1

HCID 572083194-Chloro-1-phenylpentan-3-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In two multi-injection microreactors having 4 reaction regions (each comprising one injection point, one mixing zone and one reaction zone of 1.08 mL internal reaction volume), 2-chloro propionic chloride (13.5 wt %) in tetrahydrofuran (THF, 86.5 wt %) as flow A and phenethyl-magnesium bromide (1 eq., 10 wt %) in THF (1 eq., 90 wt %) as flow B were reacted. Micro-reactor MR1 comprised internal heat exchange structures and provided a very efficient cooling (VEC) while temperature adjustment of metal microreactor MR2 was performed by submersing the microreactor in a temperature adjusted bath and provided only a low efficient cooling (LEC) between the injection points. The temperatures were displayed in table 3. Total flow rates of 20 and 40 g/min after last injection were performed. The 2nd reactant (flow B) is fed to the first reactant in a proportion corresponding to the number of inlet points. About 25 mol-% of flow B necessary to reach completion of the reaction respectively were fed at each inlet point to the first flow. After the last injection the reagents of flow B and flow A were fed in equimolar amount. The yields of the product 4-chloro-1-phenyl-pentan-3-one being collected after the respective reaction zone and quenched are shown in table 2 in relation to feed rate and cooling conditions.

Workup

  1. custom4 reaction regions (
  2. customwere reacted
  3. customMicro-reactor MR1 comprised internal
  4. customheat exchange structures and provided
  5. temperaturea very efficient cooling (VEC) while temperature adjustment of metal microreactor MR2
  6. customprovided only a low
  7. temperatureefficient cooling (LEC) between the injection points
  8. customThe 2nd reactant (flow B) is fed to the first reactant in a proportion corresponding to the number of inlet
  9. customcompletion of the reaction
  10. customrespectively were fed at each inlet

Sources & evidence

ORD record
ord-9b3040d074534e91b3e655f355d17087
Source dataset
uspto-grants-2011_05
Patent number
US07939698B2

Reaction notes

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