4-Fluorophenol → 4-Chloro-2-(4-fluorophenoxy)benzoic acid

HRID 2083768Notes

Reaction equation

HRID 2083768 reaction equation
I[C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[F:12][C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>N1C=CC=CC=1>[Cl:11][C:9]1[CH:8]=[CH:7][C:3]([C:4]([OH:6])=[O:5])=[C:2]([O:19][C:16]2[CH:17]=[CH:18][C:13]([F:12])=[CH:14][CH:15]=2)[CH:10]=1

Participants

5

Reactant 3

HCID 97324-FluorophenolHCID 11430Potassium CarbonateHCID 1394524-Chloro-2-iodobenzoic acid

Product 1

HCID 203575274-Chloro-2-(4-fluorophenoxy)benzoic acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Following the procedures outlined in Example 21, 10.7 g. (0.038 mol) of 2-iodo-4-chlorobenzoic acid, 4.3 g. (0.038 mol) of 4-fluorophenol 5.25 g. (0.038 mol) of potassium carbonate and 1.14 g. of cuprous chloride in 180 ml. of pyridine are heated under reflux overnight to give upon workup 4-chloro-2-(4-fluorophenoxy)-benzoic acid, 154°-173° C. Heating the acid (5.0 g., 0.019 mol) for one hour with 75 g. of sulfuric acid yields the corresponding 2-fluoro-6-chloro-9-xanthone, m.p. 210° C.

Workup

  1. temperatureunder reflux overnight

Sources & evidence

ORD record
ord-03a93efb2a6b48098889e1acb2791a71
Source dataset
uspto-grants-1978_04
Patent number
US04086350

Reaction notes

Loading…