Hydrochloric Acid → 7-Chloro-3-(4-ethoxy-2-fluorophenyl)-6-hydroxy-1,2-benzisoxazole

HRID 568707Notes

Reaction equation

[Cl:1][C:2]1[C:10]2[O:9][N:8]=[C:7]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH3:19])=[CH:13][C:12]=3[F:20])[C:6]=2[CH:5]=[CH:4][C:3]=1[O:21]C.Cl.N1C=CC=CC=1.Cl>CC(=O)CC>[Cl:1][C:2]1[C:10]2[O:9][N:8]=[C:7]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH3:19])=[CH:13][C:12]=3[F:20])[C:6]=2[CH:5]=[CH:4][C:3]=1[OH:21]

Participants

Conditions

Temperature: 180 °C

Procedure

A mixture of 14.2 g of 7-chloro-3-(4-ethoxy-2-fluorophenyl)-6-methoxy-1,2-benzisoxazole and pyridine hydrochloride is heated at 180° C. for 2 hr. The reaction is worked up with 2-butanone and 5% hydrochloric acid and the product crystallized from toluene to give 7-chloro-3-(4-ethoxy-2-fluorophenyl)-6-hydroxy-1,2-benzisoxazole, mp 170°-172° C. The hydroxy compound is alkylated with 0.045 mole of ethyl bromoacetate and 0.043 mole of potassium carbonate in 75 ml dimethylformamide at 65° C. for 1 hr. Workup with water gives ethyl[7-chloro-3-(2-fluoro-4-ethoxyphenyl)-1,2-benzisoxazol-6-yl]oxy}acetate, mp 118°-119° C., after recrystallization from acetonitrile.

Workup

customthe product crystallized from toluene

Sources & evidence

ORD record: ord-f9858cfcfe684bb1b136390ab91822bd
Source dataset: uspto-grants-1988_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04728662

Reaction notes

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