Acetyl chloride → Ethyl 3-(3,4-difluorophenyl)propanoate

HRID 2053586Notes

Reaction equation

HRID 2053586 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][C:11]([OH:13])=[O:12])[CH:5]=[CH:6][C:7]=1[F:8].[C:14](Cl)(=O)[CH3:15]>CCO>[F:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 27789943,4-Difluorohydrocinnamic acid

Product 1

HCID 11413226Ethyl 3-(3,4-difluorophenyl)propanoateYield 85.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 3-(3,4-difluorophenyl)propionic acid (1.0 g, 5.4 mmol) in EtOH (10 mL) is added dropwise acetyl chloride (1.0 mL, 14.1 mmol), and the solution is stirred at RT for 2 h. The solvent is rotary evaporated, and the residue purified by chromatography on silica gel; elution with heptane:EtOAc (4:1) gives 0.99 g of the product 249. 1H NMR (CDCl3) δ 7.10-6.85 (m, 3H), 4.13 (q, 2H), 2.90 (t, 2H), 3.35-2.59 (t, 2H), 1.23 (t, 2H); MS: m/z 215 (M++1).

Workup

  1. customthe residue purified by chromatography on silica gel
  2. washelution with heptane:EtOAc (4:1)

Sources & evidence

ORD record
ord-ef01f76bbcf84e4fbbf92e8f0ceabfb2
Source dataset
uspto-grants-2008_02
Patent number
US07326792B2

Reaction notes

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