2-Chloro-1-fluoro-4-nitrobenzene → 2-chloro-1-(methylsulfanyl)-4-nitrobenzene

HRID 398086

反応式

HRID 398086 の反応式
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[Cl:11].[CH3:12][S-:13].[Na+]>CN(C=O)C.C(C1C(O)=CC(C)=C(SC2C=C(C(C)(C)C)C(O)=CC=2C)C=1)(C)(C)C>[Cl:11][C:3]1[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=1[S:13][CH3:12]

参加物

5

反応物 2

HCID 676882-Chloro-1-fluoro-4-nitrobenzeneHCID 4378561Sodium methanethiolate

生成物 1

HCID 105600942-chloro-1-(methylsulfanyl)-4-nitrobenzene収率 52.3%

試薬・触媒・溶媒 2

HCID 7308Santonox触媒HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 4-fluoro-3-chloronitrobenzene (27 g, 156 mmol) in DMF (150 mL) at room temperature was added 5-tert-butyl-4-hydroxy-2-methylphenyl sulfide (100 mg) followed by sodium thiomethoxide (NaSMe) (10 g, 143 mmol) and the reaction was stirred for 6 h. The DMF was removed in vacuo and the residue was partitioned between ether (1 L) and water (1 L). The ether layer was washed with water (1 L) and brine (1 L), dried (MgSO4) and the solvent was removed under reduced pressure. The residue was purified by column chromatography (SiO2; DCM: pentane 1:5 increasing polarity to 3:7) to give the title compound (15.22 g, 49%) as a yellow solid; δH (400 MHz, CDCl3) 2.53 (3H, s), 7.20 (1H, d), 8.09 (1H, dd), 8.20 (1H, d).

後処理

  1. customThe DMF was removed in vacuo
  2. customthe residue was partitioned between ether (1 L) and water (1 L)
  3. washThe ether layer was washed with water (1 L) and brine (1 L)
  4. dry with materialdried (MgSO4)
  5. customthe solvent was removed under reduced pressure
  6. customThe residue was purified by column chromatography (SiO2; DCM: pentane 1:5 increasing polarity to 3:7)

出典と根拠

ORDレコード
ord-76eb74a912a34d528fe9645b42d50541
出典データセット
uspto-grants-2003_08
特許番号
US06610747B2

関連ノート

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