2,4-Difluorobenzaldehyde → 4-Fluoro-2-(methylthio)benzaldehyde

HRID 2214667노트

반응식

HRID 2214667 반응식
F[C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[CH3:11][S-:12].[Na+]>C1(C)C=CC=CC=1.CCOCC>[CH3:11][S:12][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5]

참가 물질

5

반응물 2

HCID 737702,4-DifluorobenzaldehydeHCID 4378561Sodium methanethiolate

생성물 1

HCID 219474094-Fluoro-2-(methylthio)benzaldehyde수율 75.3%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 3283Diethyl Ether용매

반응 조건

온도
80 °C

실험 절차

A suspension of 2,4-difluorobenzaldehyde (16 mL, 146 mmol) and sodium thiomethoxide (14 g, 200 mmol) in toluene (200 mL) was stirred at 80° C. for 7 h and 14 h at room temperature. The reaction mixture was diluted with ether (300 mL), washed with water (100 mL), saturated aqueous NaHCO3 (100 mL) and brine (50 mL). The aqueous layers were combined and extracted with ether (2×100 mL). The organic layers were combined and dried over anhydrous Na2SO4, filtered and concentrated to give a viscous oil. This viscous oil was dissolved in ether/hexanes (1:1, v/v) and slowly concentrated on under vacuum. The precipitated white solid was separated by filteration and dried to give 2-methylthio-4-fluorobenzaldehyde (18.7 g, 75% yield). 1HNMR (500 MHz, CDCl3) δ: 10.11 (1H, s), 7.78 (1H, dd, J=8.55, 6.11 Hz), 6.97 (1H, dd, J=10.07, 2.44 Hz), 6.91 (1H, td, J=8.54, 2.44 Hz), 2.45 (3H, s). MS calcd for C8H7FOS (M+H): 171.2. found: 171.6.

후처리

  1. washwashed with water (100 mL), saturated aqueous NaHCO3 (100 mL) and brine (50 mL)
  2. extractionextracted with ether (2×100 mL)
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a viscous oil
  7. concentrationv/v) and slowly concentrated on under vacuum
  8. customThe precipitated white solid was separated by filteration
  9. customdried

출처 및 근거

ORD 기록
ord-468417d2d2ab4859a7e2640bd9e1ad2d
출처 데이터셋
uspto-grants-2006_09
특허 번호
US07109186B2

반응 노트

불러오는 중…