p-Chlorothiophenol → HCID 59750905, compound
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O.[F:42][C:43]1[CH:48]=[CH:47][C:46]([F:49])=[CH:45][C:44]=1[CH:50](O)[CH2:51][CH2:52][CH2:53][CH3:54]>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH:50]([C:44]2[CH:45]=[C:46]([F:49])[CH:47]=[CH:48][C:43]=2[F:42])[CH2:51][CH2:52][CH2:53][CH3:54])=[CH:4][CH:3]=1Participants
Procedure
At 0° C., 4-chlorobenzenethiol (435 mg, 3.00 mmol), triphenylphosphine (798 mg, 3.00 mmol), and diisopropyl azodicarboxylate (588 μl, 3.00 mmol) were successively added to a solution of 1-(2,5-difluorophenyl)-1-pentanol (300 mg, 1.50 mmol) in methylene chloride (6 ml). The reaction mixture was stirred at room temperature for 15 hours, diluted with methylene chloride, and then washed successively with a 1N aqueous solution of sodium hydroxide and brine. After drying over MgSO4, the mixture was concentrated. The residue thus obtained was purified twice by medium-pressure chromatography on a silica gel column (first time with 1% ethyl acetate-hexane, and second time with hexane), whereby the title compound (266 mg, 54%) was obtained as a colorless oil.
Workup
- washwashed successively with a 1N aqueous solution of sodium hydroxide and brine
- dry with materialAfter drying over MgSO4
- concentrationthe mixture was concentrated
- customThe residue thus obtained
- customwas purified twice by medium-pressure chromatography on a silica gel column (first time with 1% ethyl acetate-hexane, and second time with hexane), whereby the title compound (266 mg, 54%)
- customwas obtained as a colorless oil
Sources & evidence
- ORD record
- ord-fee1d7d44d5345bab6179520b57b9c6c
- Source dataset
- uspto-grants-2008_07
- Patent number
- US07399775B2
Reaction notes
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