Hydrochloric Acid → {[6,7-Dichloro-2-(4-fluorophenyl)-2-methyl-1-oxo-2,3-dihydro-1H-inden-5-yl]oxy}acetic acid

HRID 1447678Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH3:21])[CH2:16][C:15]3[C:10](=[C:11]([Cl:19])[C:12]([Cl:18])=[C:13]([OH:17])[CH:14]=3)[C:9]2=[O:20])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:29][C:30]([O:32]CC)=[O:31].[OH-].[Na+].Cl>CN(C)C=O.O>[O:20]=[C:9]1[C:10]2[C:15](=[CH:14][C:13]([O:17][CH2:29][C:30]([OH:32])=[O:31])=[C:12]([Cl:18])[C:11]=2[Cl:19])[CH2:16][C:8]1([C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)[CH3:21]

Participants

Conditions

Temperature: 80 °C

Procedure

A stirred mixture of 2-(4-fluorophenyl)-2-methyl-5-hydroxy-6,7-dichloro-1-indanone (1.04 g., 0.0032 mole), potassium carbonate (0.885 g., 0.0064 mole) and ethyl bromoacetate (1.07 g., 0.0064 mole) in dimethylformamide (30 ml.) is warmed at 55°-60° C. for 3 hours, then treated with water (30 ml.)-10 N sodium hydroxide solution (1 ml., 0.01 mole) and heated at 80° C. for one hour. The reaction mixture is added slowly to water (500 ml.)-12 N hydrochloric acid (10 ml.) to precipitate 450 mg. of [1-oxo-2-(4-fluorophenyl)-2-methyl-6,7-dichloro-5-indanyloxy]acetic acid which melts at 150°-156° C. after crystallization from ethyl acetate:hexane, 1:3.

Workup

temperatureis warmed at 55°-60° C. for 3 hours
customto precipitate 450 mg
customof [1-oxo-2-(4-fluorophenyl)-2-methyl-6,7-dichloro-5-indanyloxy]acetic acid which melts at 150°-156° C. after crystallization from ethyl acetate

Sources & evidence

ORD record: ord-0a411c319abe4c19b40a978457e1fa8a
Source dataset: uspto-grants-1979_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04177285

Reaction notes

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