Methanol → 2-(4-Bromo-phenyl)-5-chloropentanoic acid methyl ester

HRID 220199Notes

Reaction equation

HRID 220199 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:12][CH2:13][CH2:14][Cl:15])[C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.[CH3:16]O>O=S(Cl)Cl>[CH3:16][O:10][C:9](=[O:11])[CH:8]([C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=1)[CH2:12][CH2:13][CH2:14][Cl:15]

Participants

4

Reactant 2

HCID 887MethanolHCID 592382802-(4-Bromophenyl)-5-chloro-pentanoic acid

Product 1

HCID 592382962-(4-Bromo-phenyl)-5-chloropentanoic acid methyl esterYield 90%

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

To a solution of 2-(4-Bromo-phenyl)-5-chloropentanoic acid (3 g, 10.38 mmol) in MeOH (60 mL), SOCl2 (2 mL) was added at 0 degrees Celsius, then the mixture refluxed for 5 h. After cooling, the solution was evaporated to dryness under reduced pressure, then EtOAc was added and the mixture was washed with aq. NaHCO3, the organic layer was dried with MgSO4, and evaporated to give the compound as an oil (2.85 g, 90%). MS: calc'd 304 (MH+), exp 304 (MH+).

Workup

  1. temperaturethe mixture refluxed for 5 h
  2. temperatureAfter cooling
  3. customthe solution was evaporated to dryness under reduced pressure
  4. additionEtOAc was added
  5. washthe mixture was washed with aq. NaHCO3
  6. dry with materialthe organic layer was dried with MgSO4
  7. customevaporated

Sources & evidence

ORD record
ord-29d22aa1221447b0b06b96161033fd5f
Source dataset
uspto-grants-2012_06
Patent number
US08202866B2

Reaction notes

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