Ishihara Sangyo Kaisha, Ltd.

Hayato Ariyoshi

Hiroshi Yoshizawa

Rikuo Nasu

Tadashi Nakamura

Tatsuo Isogai

Takayoshi Ando

Koji Hayashi

Motohiko Hamaguchi

Isamu Katsuyama

Sho Tokumoto

Masaru Kimura

Masahiko Sawaki

A method for producing 2-methylspiro(1,3-oxathiolane-5,3')quinuclidine, which comprises reacting 3-hydroxy-3-mercaptomethylquinuclidine or a salt thereof and a carbonyl compound in the presence of a catalyst made of at least one member selected from the group consisting of tin halides, oxyacids of phosphorus, phosphorus oxyhalides and organic sulfonic acids, to produce cis-form 2-methylspiro(1,3-oxathiolane-5,3')quinuclidine or a salt thereof.

Method for producing 2-methylspiro(1,3-oxathiolane-5,3')quinuclidine

A method for halogenating an aromatic compound, which comprises reacting the aromatic compound of the formula (I): ##STR1## wherein X is a hydroxyl group, an amino group or an acylamino group, each of Z.sub.1 and Z.sub.2 is a hydrogen atom or a halogen atom, one of R and Y is a hydrogen atom and the other is a nitro group, a cyano group or a trifluoromethyl group, and Q is a nitrogen atom or --C(T).dbd. (wherein T is a hydrogen atom, a halogen atom, a nitro group, a cyano group or a trifluoromethyl group), with a halogenating agent to obtain a 3-halogenoaromatic compound of the formula (II): ##STR2## wherein one of R' and Y' is a halogen atom and the other is a nitro group, a cyano group or a trifluoromethyl group, and X, Z.sub.1, Z.sub.2 and Q are as defined above.

Method for halogenating an aromatic compound

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Yokkaichi, Japan

Hayato Ariyoshi