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

HRID 1874692노트

반응식

HRID 1874692 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 457907333,6-Difluoro-2-methoxybenzonitrile수율 91%

시약·촉매·용매 1

HCID 887Methanol용매2회

실험 절차

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%)

후처리

  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.

출처 및 근거

ORD 기록
ord-6bf40cd67b404c73b16d62e5f4c7ac61
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08304446B2

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