p-Toluenesulfonic acid → 2-Bromo-4-fluoro-1-(methoxymethoxy)benzene

HRID 252230노트

반응식

HRID 252230 반응식
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[OH:9].C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH3:21][O:22][CH2:23]OC>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[O:9][CH2:21][O:22][CH3:23]

참가 물질

5

반응물 3

HCID 6101p-Toluenesulfonic acidHCID 8020DimethoxymethaneHCID 6054722-Bromo-4-fluorophenol

생성물 1

HCID 220325852-Bromo-4-fluoro-1-(methoxymethoxy)benzene

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 2-bromo-4-fluoro-phenol (1 g, 5.23 mmol) in CH2Cl2 (120 mL) was added p-toluenesulphonic acid (0.07 g, mmol), dimethoxymethane (2.31 mL, 26.15 mmol) and the resulting mixture was heated under reflux for 16 h under a soxhlett apparatus charged with freshly dried molecular 4 Å sieves. The reaction was allowed to warm to room temperature and washed with 2M sodium hydroxide (100 mL) then dried (Na2SO4), filtered and the solvent was evaporated under vacuum to give title compound as an oil: 0.567 g, 46%. 1H-NMR (CDCl3, 300 MHz) δ7.31 (dd, 1H, J=2.9, 7.9 Hz, ArH), 7.13 (dd, 1H, J=4.9, 9.1 Hz, ArH), 6.98 (m, 1H, ArH), 5.21 (s, 2H, —OCH2O—), 3.54 (s, 3H, —OCH3)

후처리

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 16 h under a soxhlett apparatus
  3. additioncharged with freshly dried molecular 4 Å
  4. washwashed with 2M sodium hydroxide (100 mL)
  5. dry with materialthen dried (Na2SO4)
  6. filtrationfiltered
  7. customthe solvent was evaporated under vacuum

출처 및 근거

ORD 기록
ord-3cfc19f41b774540bdf7178be25e68e1
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07868032B2

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