Benzenethiol, 2-(1-methylethyl)- → 5-(2-Isopropylphenylthio)furan-3-carboxylic Acid

HRID 894240Notes

Reaction equation

HRID 894240 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[SH:10])([CH3:3])[CH3:2].Br[C:12]1[O:16][CH:15]=[C:14]([C:17]([OH:19])=[O:18])[CH:13]=1>>[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10][C:12]1[O:16][CH:15]=[C:14]([C:17]([OH:19])=[O:18])[CH:13]=1)([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 96003Benzenethiol, 2-(1-methylethyl)-HCID 133335605-Bromofuran-3-carboxylic acid

Product 1

HCID 211624585-(2-Isopropylphenylthio)furan-3-carboxylic Acid

Procedure

Following the procedure of Example 9, o-isopropylthiophenol [4.77 g., 31.4 mmoles; Hansch and Blondon, J. Am. Chem. Soc. 70, 1561 (1948)] was reacted with 5-bromofuran-3-carboxylic acid. Rather than recover the initial crude product by filtration, the mixture was reextracted with ethyl acetate, the ethyl acetate back-washed with water and saturated brine, dried over anhydrous sodium sulfate and evaporated to yield crude product. Recrystallization from hexane produced purified 5-(2-isopropylphenylthio)furan (785 mg., m.p. 117°-120° C., m/e 262).

Workup

  1. customRather than recover the initial crude product
  2. filtrationby filtration
  3. washthe ethyl acetate back-washed with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated
  6. customto yield crude product
  7. customRecrystallization from hexane
  8. customproduced
  9. custompurified 5-(2-isopropylphenylthio)furan (785 mg., m.p. 117°-120° C., m/e 262)

Sources & evidence

ORD record
ord-4e956bf54ad04a3fbb525b78d33cec1f
Source dataset
uspto-grants-1981_08
Patent number
US04282246

Reaction notes

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