82455-06-9 → Methyl 3-(4-fluorophenyl)propanoate

HRID 647430Notes

Reaction equation

HRID 647430 reaction equation
Br[CH:2]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=1)[C:3]([O:5][CH3:6])=[O:4]>C(O)(=O)C.[Zn]>[F:14][C:11]1[CH:10]=[CH:9][C:8]([CH2:7][CH2:2][C:3]([O:5][CH3:6])=[O:4])=[CH:13][CH:12]=1

Participants

4

Reactant 1

HCID 1218868382455-06-9

Product 1

HCID 22906572Methyl 3-(4-fluorophenyl)propanoate

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

Crude methyl 2-bromo-3-(4-fluorophenyl)propionate in acetic acid (330 ml) was stirred and treated with zinc dust (32.75 g) in portions over 30 minutes. The mixture was stirred for an additional 30 minutes and filtered, and the filter cake was washed with acetic acid. After the filtrate was evaporated the residue was partitioned between methylene chloride and water to give crude methyl 3-(4-fluorophenyl)propionate, which was refluxed with aqueous sodium hydroxide (400 ml, 10%) for 2 hrs, cooled, treated with decolorizing carbon, and filtered. The filtrate was acidified with 5 N HCl and filtered. The filter cake was washed extensively with water to give 3-(4-fluorophenyl)propionic acid (20.0 g) as colourless crystals, mp 90° C.

Workup

  1. filtrationfiltered
  2. washthe filter cake was washed with acetic acid
  3. customAfter the filtrate was evaporated the residue
  4. customwas partitioned between methylene chloride and water

Sources & evidence

ORD record
ord-d68543213f61443bad84c49c21c173eb
Source dataset
uspto-grants-1983_10
Patent number
US04409017

Reaction notes

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