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Trifluoroacetic anhydride → 2-Fluoro-3-methoxy-5-methylbenzenethiol

HRID 591443
ノート
印刷プレビュー

反応式

HRID 591443 の反応式
[F:1][C:2]1[C:7]([S:8](C)=O)=[CH:6][C:5]([CH3:11])=[CH:4][C:3]=1[O:12][CH3:13].C(OC(C(F)(F)F)=O)(C(F)(F)F)=O>CC#N>[F:1][C:2]1[C:3]([O:12][CH3:13])=[CH:4][C:5]([CH3:11])=[CH:6][C:7]=1[SH:8]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 9845Trifluoroacetic anhydrideHCID 897676932-Fluoro-1-methoxy-5-methyl-3-(methylsulfinyl)benzene

生成物 1

HCID 897676722-Fluoro-3-methoxy-5-methylbenzenethiol収率 51.7%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
0 °C

実験手順

To a mixture of 2-fluoro-1-methoxy-5-methyl-3-(methylsulfinyl)benzene (486 mg) and CH3CN (20 mL) was added TFAA (1.02 mL) at 0° C. The mixture was stirred at 0° C. for 1 h, and concentrated in vacuo. The residue was dissolved in a mixture of MeOH (3.5 mL) and TEA (3.5 mL) at 0° C. The solution was stirred at room temperature for 1 h, and concentrated in vacuo. The residue was diluted with saturated aqueous NH4Cl, and the mixture was extracted with EtOAc. The organic layer was extracted with 1N NaOH. The aqueous layer was acidified with 1N HCl and extracted with EtOAc. The combined organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo to give the title compound (214 mg).

後処理

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in a mixture of MeOH (3.5 mL) and TEA (3.5 mL) at 0° C
  3. stirringThe solution was stirred at room temperature for 1 h
  4. concentrationconcentrated in vacuo
  5. additionThe residue was diluted with saturated aqueous NH4Cl
  6. extractionthe mixture was extracted with EtOAc
  7. extractionThe organic layer was extracted with 1N NaOH
  8. extractionextracted with EtOAc
  9. washThe combined organic layer was washed with brine
  10. dry with materialdried over MgSO4
  11. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-ea7f7ee883d241b3b60d95f0f3c2670a
出典データセット
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09238639B2

反応ノート

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