2,3,6-Trifluorobenzonitrile → 3,6-Difluoro-2-methoxybenzonitrile

HRID 1808586ノート

反応式

HRID 1808586 の反応式
[Na].[CH3:2][O-:3].[Na+].F[C:6]1[C:13]([F:14])=[CH:12][CH:11]=[C:10]([F:15])[C:7]=1[C:8]#[N:9]>CO>[F:14][C:13]1[C:6]([O:3][CH3:2])=[C:7]([C:10]([F:15])=[CH:11][CH:12]=1)[C:8]#[N:9]

参加物

5

反応物 3

HCID 1456222,3,6-TrifluorobenzonitrileHCID 5360545SodiumHCID 10942334Sodium Methoxide

生成物 1

HCID 457907333,6-Difluoro-2-methoxybenzonitrile収率 91%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

実験手順

Methanol (600 mL) was treated portionwise with sodium (Alfa, 16.1 g, 0.702 gatoms, 1.05 equiv.). The sodium methoxide solution was cooled to room temperature and added dropwise to a solution of 2,3,6-trifluorobenzonitrile (Matrix, 105 g, 0.699 mol) in methanol (600 ml) at room temperature. After addition was complete the mixture was stirred for 1 hour at room temperature before removing the methanol under reduced pressure. The residue was partitioned between diethyl ether (500 ml) and water (500 mL). The organic layer was removed, dried over MgSO4, filtered and evaporated to give the crude product. This was purified by distillation using a 6″ vigreux column @ 20 mmHg, oil bath 160° C., head temp 120° C. to give the title compound as a white solid (108 g, 91%)

後処理

  1. additionAfter addition
  2. custombefore removing the methanol under reduced pressure
  3. customThe residue was partitioned between diethyl ether (500 ml) and water (500 mL)
  4. customThe organic layer was removed
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customto give the crude product
  9. distillationThis was purified by distillation
  10. custom20 mmHg, oil bath 160° C., head temp 120° C.

出典と根拠

ORDレコード
ord-d591a075a93646588361f6f93715a298
出典データセット
uspto-grants-2013_01
特許番号
US08357716B2

反応ノート

読み込み中…