Hydrochloric Acid → 3-Chloro-5-methoxybenzonitrile

HRID 602585

반응식

HRID 602585 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8](Cl)[CH:9]=1)[C:5]#[N:6].[CH3:11][O-:12].[Na+].Cl>CN(C=O)C>[Cl:1][C:2]1[CH:9]=[C:8]([O:12][CH3:11])[CH:7]=[C:4]([CH:3]=1)[C:5]#[N:6]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 810523,5-DichlorobenzonitrileHCID 10942334Sodium Methoxide

생성물 1

HCID 219499213-Chloro-5-methoxybenzonitrile수율 86.5%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

step 1—A 100 ml round bottom flask was charged under a stream of nitrogen with 3,5-dichlorobenzonitrile (R-3a,7.0 g, 40.69 mmol) and anhydrous DMF (75 mL). To the solution was added sodium methoxide (2.26 g, 44.76 mmol) and resulting solution was stirred further at RT for 24 h. When the reaction was complete, aqueous 10% HCl added dropwise to the reaction vessel. The crude mixture was extracted with EtOAc and sequentially washed with aqueous acid, water and brine. The EtOAc extracts were dried (Na2SO4), filtered and the solvent was removed in vacuo to afford a crude solid which was recrystallized from hexane/acetone to afford 5.9 g (86%) of 5-chloro-3-methoxy-benzonitrile.

후처리

  1. customresulting solution
  2. extractionThe crude mixture was extracted with EtOAc
  3. washsequentially washed with aqueous acid, water and brine
  4. dry with materialThe EtOAc extracts were dried (Na2SO4)
  5. filtrationfiltered
  6. customthe solvent was removed in vacuo
  7. customto afford a crude solid which
  8. customwas recrystallized from hexane/acetone

출처 및 근거

ORD 기록
ord-7f8e5d2ac95b4b8ba3b792073f11181f
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07906540B2

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