Oxalyl chloride → (4-Fluorophenoxy)acetyl chloride
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]=1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
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
- concentrationthe mixture was concentrated under vacuum
Sources & evidence
- ORD record
- ord-1ca09f8bcc1d4bd88e7a387e5b9baae2
- Source dataset
- uspto-grants-2007_05
- Patent number
- US07223798B2
Reaction notes
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