2-(3,4-Dichlorophenoxy)-5-fluorobenzaldehyde → 2-(3,4-Dichlorophenoxy)-5-fluoro-benzoic acid

HRID 6900

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][C:17]=1[Cl:18])[O:5][C:6]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][C:7]=1[CH:8]=[O:9].CC(C)=[O:21].OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][C:17]=1[Cl:18])[O:5][C:6]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][C:7]=1[C:8]([OH:21])=[O:9]

Participants

Conditions

Temperature: 25 °C

Procedure

Alternatively, a solution of 4.28 g (15 mmol) of 2-(3,4-dichloro-phenoxy)-5-fluorobenzaldehyde (Preparation no. 5) in 25 mL of acetone was cooled to 5–10° C. and treated via syringe with 5.8 mL (15.6 mmol) of 2.67 M Jones reagent*. After 1 hr at this temperature, the reaction was quenched with 8 mL of isopropanol, allowed to warm to 25° C., and filtered through a pad of d.e. The filtrate was concentrated in vacuo to approximately ¼ volume, diluted with water and extracted several times with CHCl3. The organic layers were washed with water, then with saturated NaCl and finally dried over MgSO4 and concentrated to provide 2-(3,4-dichlorophenoxy)-5-fluoro-benzoic acid as a tan solid, 4.19 g. 1H-nmr (CDCl3, 400 MHz, δ): 7.78 (dd, 1H), 7.38 (d, 1H), 7.27 (m, 1H), 6.98 (m, 2H), 6.81 (dd, 1H). *Jones reagent was prepared from 13.4 g of chromium trioxide and 11.5 mL of concentrated H2SO4, diluted to a final volume of 50 mL with H2O.

Workup

customthe reaction was quenched with 8 mL of isopropanol
filtrationfiltered through a pad of d.e
concentrationThe filtrate was concentrated in vacuo to approximately ¼ volume
additiondiluted with water
extractionextracted several times with CHCl3
washThe organic layers were washed with water
dry with materialwith saturated NaCl and finally dried over MgSO4
concentrationconcentrated

Sources & evidence

ORD record: ord-d3006829c64043e1abcf88cb05d868f9
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07084165B2

Linked notes

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