Oxalyl chloride → (4-Fluorophenoxy)acetyl chloride

HRID 2078498Notes

Reaction equation

HRID 2078498 reaction equation
[C:1]([Cl:6])(=[O:5])[C:2](Cl)=[O:3].[F:7][C:8]1[CH:18]=[CH:17][C:11](OCC(O)=O)=[CH:10][CH:9]=1>CN(C)C=O.ClCCl>[F:7][C:8]1[CH:18]=[CH:17][C:11]([O:3][CH2:2][C:1]([Cl:6])=[O:5])=[CH:10][CH:9]=1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 678824-Fluorophenoxyacetic acid

Product 1

HCID 2759057(4-Fluorophenoxy)acetyl chlorideYield 100.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

Oxalyl chloride (60 mL, 686 mmol) and dimethylformamide (DMF) (8 drops, cat.) were added to a stirred suspension of 2-(4-fluorophenoxy)ethanoic acid (97.3 g, 572 mmol) in dichloromethane (500 mL). After 22 hours, the mixture was concentrated under vacuum to obtain 108 g of 2-(4-fluorophenoxy)ethanoic acid chloride, a compound of formula (Y), as a yellow oil in quantitative yield; 1H NMR (CDCl3) δ 4.90 (s, 2H), 6.84 (m, 2H), 6.99 (m, 2H) ppm.

Workup

  1. concentrationthe mixture was concentrated under vacuum

Sources & evidence

ORD record
ord-b64780f9b7db415db3689fa8f216ebc6
Source dataset
uspto-grants-2011_04
Patent number
US07928255B2

Reaction notes

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