Dimethyl Disulfide → 5-(2-Cyano-4-fluorophenoxy)-2-methylthiophenol

HRID 325830노트

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HRID 325830 반응식
[C:1]([C:3]1[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:4]=1[O:5][C:6]1[CH:7]=[C:8]([OH:12])[CH:9]=[CH:10][CH:11]=1)#[N:2].[CH3:18][S:19]Cl.[CH3:21][S:22]SC.ClCl>C(Cl)Cl>[C:1]([C:3]1[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:4]=1[O:5][C:6]1[CH:11]=[CH:10][C:9]([CH3:8])=[C:18]([SH:19])[CH:7]=1)#[N:2].[C:1]([C:3]1[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:4]=1[O:5][C:6]1[CH:11]=[CH:10][C:9]([S:22][CH3:21])=[C:8]([OH:12])[CH:7]=1)#[N:2]

참가 물질

7

반응물 4

HCID 12232Dimethyl DisulfideHCID 24526ChlorineHCID 138595MethanesulfenylchlorideHCID 204628423-(2-Cyano-4-fluorophenoxy)phenol

생성물 2

HCID 204628345-(2-Cyano-4-fluorophenoxy)-2-methylthiophenolHCID 204628495-(2-Cyano-4-fluorophenoxy) 2-(methylthio)phenol

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

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온도
-20 °C

실험 절차

3-(2-Cyano-4-fluorophenoxy)phenol (0.1 mole) and methylene chloride (200 ml) are charged into a glass reaction vessel equipped with a mechanical stirrer and addition funnel. The mixture is stirred until dissolved and cooled to about -20° C. A solution of methyl sulfenyl chloride freshly prepared by reacting dimethyl disulfide (0.15 mole) with chlorine (0.18 mole) in methylene chloride (100 ml) is then added dropwise to the reaction vessel over a period of about 40 minutes. After the addition is completed stirring is continued for 30 minutes with cooling and 30 minutes at room temperature. After this time the reaction mixture is washed with water (200 ml) with 5% aqueous sodium bicarbonate (200 ml) and again with water (200 ml). The washed solution is then dried by passing it through a phase separator. The dried solution is stripped of solvent under reduced pressure and the residue chromatographed using a clay column and hexane/ethyl acetate as the eluant. The fractions containing the product are combined and stripped of solvent to yield the desired product 5-(2-cyano-4-fluorophenoxy) 2-(methylthio)phenol as the residue.

후처리

  1. customequipped with a mechanical stirrer and addition funnel
  2. dissolutionuntil dissolved
  3. additionis then added dropwise to the reaction vessel over a period of about 40 minutes
  4. additionAfter the addition
  5. stirringis completed stirring
  6. temperaturewith cooling and 30 minutes at room temperature
  7. washAfter this time the reaction mixture is washed with water (200 ml) with 5% aqueous sodium bicarbonate (200 ml) and again with water (200 ml)
  8. customThe washed solution is then dried
  9. customthe residue chromatographed
  10. additionThe fractions containing the product

출처 및 근거

ORD 기록
ord-9bd8d7f06934470fbb7d5f2a826628a1
출처 데이터셋
uspto-grants-1984_04
특허 번호
US04443248

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