3-(Trifluoromethyl)benzenethiol → HCID 21162545, compound

HRID 894251Notes

Reaction equation

HRID 894251 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[C:5]([SH:9])[CH:6]=[CH:7][CH:8]=1.Br[C:13]1[O:17][CH:16]=[C:15]([C:18]([OH:20])=[O:19])[CH:14]=1>>[F:11][C:2]([F:1])([F:10])[C:3]1[CH:4]=[C:5]([S:9][C:13]2[O:17][CH:16]=[C:15]([C:18]([OH:20])=[O:19])[CH:14]=2)[CH:6]=[CH:7][CH:8]=1

Participants

3

Reactant 2

HCID 1367513-(Trifluoromethyl)benzenethiolHCID 133335605-Bromofuran-3-carboxylic acid

Product 1

HCID 21162545HCID 21162545, compound

Procedure

By the procedure of Example 13, m-trifluoromethylthiophenol (5.59 g., 31.4 mmoles) was reacted with 5-bromofuran-3-carboxylic acid. Isolation according to Example 16 gave crude product (1.0 g.) as a gummy solid. The latter was chromatographed on silica gel with ethyl acetate-1/hexane-5/5% acetic acid as eluant. Clean middle fractions were combined and evaporated to solid product (550 mg.). Recrystallization from hexane gave purified 5-(3-trifluoromethylphenylthio)furan-3-carboxylic acid (310 mg., m.p. 99°-101° C., m/e 288).

Sources & evidence

ORD record
ord-aed3dd421508484c878f7bc0428fdf54
Source dataset
uspto-grants-1981_08
Patent number
US04282246

Reaction notes

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