Preparation of 4-nitrothioanisole

Details Preparation of 4-nitrothioanisole Preparation of 4-nitrothioanisole

1980-01-09

1981-11-03

Daus, Donald G.

Organic compounds -- part of the class 532-570 series

Organic compounds

Sulfur containing

C07C14932

Patent

active

042987610

ABSTRACT:
A process for the preparation of 4-nitrothioanisole comprising successively in a single vessel and without intermediate isolation reacting 4-nitrochlorobenzene with Na.sub.2 S.sub.2, then with an alkaline Na.sub.2 S solution and with a methylating agent. Advantageously the reactions are effected in methanol or aqueous methanol, the reactions with Na.sub.2 S.sub.2 and Na.sub.2 S are carried out at a temperature between about 50.degree. to 70.degree. C., the Na.sub.2 S.sub.2 is formed in situ in about 20% excess from Na.sub.2 S and sulphur, the Na.sub.2 S solution is rendered alkaline with sodium methylate or sodium hydroxide, and methylation is effected with methyl chloride at about 27.degree. to 35.degree. C. The product is produced in such high yield and purity that it can be employed directly for chlorination, without extensive purification, to produce insecticide intermediates.

REFERENCES:
S. Morris et al., JACS, 68, No. 3 (1946).
Berichte der Deutschen Chemischen Gesellschaft, III, (1909), 3466.
C. C. Price et al., J. Am. Chem. Soc. 68, 498 (1946).
Yagupolski et al., J. Gen. Chem. USSR (1952).
K. Brand, Chem. Ber. 42, 3463 (1909).

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