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

HRID 252230ノート

反応式

HRID 252230 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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)

後処理

  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

出典と根拠

ORDレコード
ord-3cfc19f41b774540bdf7178be25e68e1
出典データセット
uspto-grants-2011_01
特許番号
US07868032B2

反応ノート

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