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

HRID 398086

반응식

HRID 398086 반응식
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]

참가 물질

5

반응물 2

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

생성물 1

HCID 105600942-chloro-1-(methylsulfanyl)-4-nitrobenzene수율 52.3%

시약·촉매·용매 2

HCID 7308Santonox촉매HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-76eb74a912a34d528fe9645b42d50541
출처 데이터셋
uspto-grants-2003_08
특허 번호
US06610747B2

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